A Slack Story Podcast

Money as MacGuffin: Playing the Tech Lottery GameJames Sherrett reflects on a career largely shaped by the “tech lottery game” of compensation: salary plus stock options. He spent his early work years in late-1990s online finance media, then in roles helping companies adapt to the internet, then six years running a startup that failed. What did he learn? He declines to disclose his Slack earnings. A number is less interesting than understanding how the game works. Then he describes how outcomes of the Tech Lottery Game vary based on factors like teammates, investors, fundraising strength, and especially cap tables (share counts, ownership distribution, liquidation preferences, and complex clauses). He compares Slack’s cap table and $27.7B Salesforce acquisition with Mobify’s tangled cap table. He concludes that money is a startup “MacGuffin.” Day-to-day motivation came from teammates, customers, and doing quality work.00:00 Money And startups01:25 Salary plus options02:15 No upside to sharing numbers03:29 Learning the Tech Lottery Game05:09 Spotting rocket ships06:07 Cap table basics08:06 Comparing two acquisition outcomes09:23 Champagne Problems10:53 Money as MacGuffin12:43 What really motivates14:50 Thank you very much This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Questions That Remain: Luck, Culture vs People, Leaving Before It’s TimeJames Sherrett reflects on unresolved questions from A Slack Story: the role of luck in Slack’s and his own success, culture versus people as drivers of performance, and how to leave before it’s time by building a life to move toward. He argues luck is unknowable but significant. He quotes Michael Lewis on success being rationalized and luck creating obligation to the unlucky. He notes Slack benefited from launching at the right moment amid enabling technologies and market conditions. On culture versus people, he rejects a zero-sum framing, describing a reinforcing cycle where great people build culture and culture attracts great people. He recounts growing less motivated by Slack’s scale and achievements, defining new goals largely outside work. He tells a pre-pandemic story that helped with his decision to leave and plan life after Slack.01:38 Luck in Slack's success04:26 Luck lessons in life06:34 Culture versus people is the wrong framing08:26 People build the flywheel09:35 Leaving before it's time10:54 Seeking a life after Slack12:28 Farewell to all that This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Thank You Slack: Seven Years From Employee #9 to a Global CompanyJames Sherrett reflects on leaving Slack on June 5, 2020, exactly seven years after joining as the ninth employee, during which Slack grew from $0 revenue and eight employees to over 2,200 employees in 16 offices and nearly $1B in revenue as a NYSE-listed company. He recounts early marketing and positioning work (“Be less busy”), the 2013 invite launch that drew 8,000 signups in 24 hours, early customer development and support, and the shift into account management and the 2014 paid launch with credits, invoicing, and the “Fair Billing Policy.” He describes building teams, opening Slack’s EMEA office in Dublin in 2015, and later leading Executive Briefing Centres and Innovation Tours. He leaves to prioritize the rest of his life, pursuing advisory work, writing, personal projects, and volunteering.00:00 A farewell to Slack02:06 Why I had to leave04:22 Thank You, Slack letter05:36 Joining as marketer06:49 Positioning Be less busy07:55 Launch day signups09:00 Customer feedback loop14:00 Saying No Nicely17:35 Account Management begins17:55 Paid launch and billing20:35 Offsite, swag and scale22:44 Enterprise sales emerges25:00 Building the Dublin office28:54 Culture and hiring in EMEA32:39 Scaling EMEA sales34:35 Executive Briefing Centers35:52 Innovation Tours program38:35 Gratitude and next chapter41:35 Final reflections and farewell This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Slack Frontiers, Almost Getting PIP’d, and Accepting Less AmbitionJames Sherrett continues A Slack Story with 3 stories he hadn't told yet. First, how Slack launched its customer conference, Frontiers, starting in 2017 after customers began asking for it. He explains how the conference brought together customers, partners, product, and the Slack team, and how it created business urgency by serving as a deadline, including an on-site executive briefing program by 2019. He shares vivid details from Frontiers and the event’s “Frontiers” name inspiration from a Carl Sagan quote about humanity needing a frontier, noting omitted lines about knowing how to reach “a new world next door.” Second, he recounts a January 2020 warning from his boss, Marnie, that he was trending toward a performance improvement plan. Third, Sherrett reflects on accepting less ambition as he played smaller roles as Slack hired world-class experts to replace functions he initially led. He reframing his trajectory as a generalist pioneer who starts new initiatives until others can do them better. He emphasizes humility, change (“burn the metaphorical boats”), and the value of never underestimating sheer gall. He closes with some thoughts about self-awareness, challenge and selling out to do be the best you possible.00:00 Intro and Feedback00:40 Why companies host conferences01:44 Building Slack Frontiers03:09 Frontiers moments and meaning05:11 Almost on a PIP06:38 Resetting from complacency07:37 Learning to accept less ambition10:20 A generalist mindset12:26 Never underestimate sheer gall14:06 Finding some self awareness This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Going Public from Yellowstone: Slack’s NYSE Debut and the Reality of ChangeJames Sherrett recounts Slack’s direct public offering (DPO) on June 20, 2019, when shares began trading on the New York Stock Exchange under the ticker WORK, roughly five years after Slack’s first revenue and at a valuation north of $20 billion. Instead of being in New York, he was on a family trip in West Yellowstone with spotty internet, balancing work with family. He describes placing insider sell orders the night before, the DPO mechanics versus an IPO (including immediate insider trading flexibility but greater pricing uncertainty), and a launch-morning panic when his orders hadn’t saved. After spending the day offline biking and exploring with his son, he later catches up on headlines and teammate photos from the NYSE. Sherrett shares Butterfield’s framing of going public as a rite of passage rather than the journey’s peak, then reflects on questions he later received about whether money changed Slack, noting it did through growth, new people, increased conservatism, and intensified competition (especially with Microsoft Teams), while much of Slack’s spirit and customer focus remained. He concludes that the changes weren’t all positive but were overwhelmingly so from his perspective, and teases future stories about finding frontiers, and accepting less ambition.00:00 Slack goes public as WORK01:28 Choosing Yellowstone over the NYSE: family, FOMO, and the trip out03:28 The night before: placing orders and feeling the stakes04:13 DPO vs IPO: why Slack took the direct listing route06:09 Launch morning panic: scrambling and the opening bell07:13 Wall Street movie moment: how the price of WORK got set08:51 Unreal meets reality: orders fill and WORK starts trading10:06 Offline celebration: bikes, rivers, and a day away from the news13:03 Did money change Slack?15:47 Closing thoughts: next on the journey This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

The Pocket Square Project: Swag off in all directionsIn this episode, James Sherrett shares how he created unconventional company swag for Slack. From initial inspiration at Heathrow Airport to collaborating with suppliers and distributing pocket squares as multi-purpose swag, he explores the impact and reception of these stylish silk squares. This off-the-books project showcases the playfulness and high standards Slack aspired to in its executive programs. Sherrett reflects on the innovative culture at Slack, the sense of autonomy, and the joy of injecting a sense of play into his work, all while hinting at future episodes on significant milestones like Slack's public offering.00:00 Introduction: A Slack Story by James Sherrett00:05 The birth of the pocket square idea00:43 Finding the right design01:51 Partnering with Monsoon Corporate Gifts02:43 The arrival and reactions03:24 Covert Marketing operations04:07 Spreading the pocket squares06:06 Broader swag strategy06:55 Standards and challenges08:50 Conclusion: embracing play and change This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Harnessing Innovation: Slack's Journey to Innovation ToursJames Sherrett narrates the journey of how Slack capitalized on the rising demand for Innovation Tours, turning it into a valuable business opportunity. Initially uncertain about the concept, Slack learned that Innovation Tours vary greatly, with companies, government agencies, consulting firms, and specialized tour companies organizing them. By assessing the benefits of these tours through a decision matrix, Slack hosted tailored visits, sharing their company culture and innovative practices. These tours increased visibility and led to significant business deals. Ultimately, the Innovation Tours fostered collaboration and showcased Slack as a leader in enabling organizational change.00:00 Introduction: A Slack Story by James Sherrett00:19 The concept of Innovation Tours00:54 Understanding the demand for Innovation Tours01:48 Different types of Innovation Tours03:26 The value of Innovation Tours?05:19 Slack's approach to Innovation Tours06:53 A decision matrix for Innovation Tours09:37 A memorable Innovation Tour experience14:53 Lessons from Building a Culture of Innovation18:37 The Impact of Innovation Tours This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Reinventing Meetings: The Power of Effective Executive BriefingsJames Sherrett discusses some common frustrations with meetings and argues for their potential efficiency when conducted properly. By exploring Slack's approach to transforming meetings into executive briefings, he demonstrates how thoughtful execution can drive business success. He highlights the collaboration between Slack's sales teams, Slack executives, and Slack customers to create effective briefings that help close deals. Key results of Slack's briefing process include a higher win rate for deals and significant contributions to annual contract value.00:00 Introduction: the dreaded meeting00:57 The case for effective meetings01:23 Human nature and meetings03:31 Steps to better ,eetings05:04 Reinventing meetings as briefings05:44 Collaborating with our 3 key groups08:08 Examples of successful briefings13:37 Results and reflections15:33 Conclusion: finding competitive advantages in plain sight This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Fumbling Towards Legitimacy: A Senior Technology Strategist at SlackJames Sherrett shares his journey of becoming a Senior Technology Strategist at Slack, a role he describes as initially undefined and nebulous. He recounts how he took on the challenge of defining his new role, like with his previous positions at the company. Sherrett outlines the three primary responsibilities he eventually took on: executive briefing center engagements, investor and partner engagements, and innovation tours. Were there personal and professional hurdles? Some. Frequent travel and the need for self-sufficiency on the road. Sherrett's tries to capture the nuance of becoming 'the Slack man' though he never talked about it. He highlights the importance of presenting a coherent future vision, drawing from experiences and lessons in executive engagement. The episode concludes with a teaser on exploring these executive briefings and the balance between vision and reality.00:00 Introduction: becoming a Senior Technology Strategist01:19 Defining the role: challenges and opportunities02:28 Establishing the hob: Executive Briefings and public speaking03:11 A Portfolio of Activities04:49 Embracing the Slack Man identity06:38 Life on the road and time alone09:40 Changing beliefs and behaviors11:59 Selling the Future: lessons from Microsoft13:36 Conclusion: Working on Slack vision for the future This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Returning to Slack YVR: A Journey HomeJames Sherrett recounts his return to Vancouver and Slack YVR on Canada Day, 2017. Slack YVR is familiar yet changed, with growth from 1 to 3 floors. We spend some time on the exceptional team that made Slack special, the culture, shared mission, and collaboration that fostered excellence within Slack. Key employees advanced within the company. How Slack YVR uniquely provided perspective and a focus on deeper work.00:00 Returning to Vancouver: a new beginning02:40 Settling back into Slack YVR04:25 The people of Slack: at the heart of the company07:37 Growth and expansion: Slack's global journey10:18 Balancing work and travel11:39 Building new programs and enjoying the work This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Discovering Executive Programs by Doing Executive ProgramsAfter years of team management, James Sherrett finds himself reporting directly to a new, new, new, new boss, Marnie, while no longer managing a team. This transition leads James to explore the world of Executive Programs and Executive Briefing Centres (EBCs), specialized facilities for hosting executives. James learns to adapt to his new role, focusing on building relationships within sales teams, speaking at various industry conferences, and running executive briefing sessions to advance Slack's business goals. Throughout the script, James highlights key strategies, such as thorough preparation for meetings and public speaking engagements, and emphasizes the importance of learning by doing, illustrating his journey from Dublin to various global cities to advance Slack's outreach and impact.00:05 New boss, new role: adjusting to changes02:02 Embracing the essentials and finding core responsibilities02:59 A tour through Executive Programs07:29 Public speaking and representing Slack09:49 The pickle of setting: work and location not aligning15:08 Learning by coing: leading EBCs in London17:50 Conclusion: returning to Vancouver This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Reflections on an Irish Adventure: Transitions and Changes at SlackJames Sherrett shares his experience working at Slack and living in Ireland from 2015 to 2017, highlighting both personal and societal changes. He observes Ireland's transformation with the legalization of same-sex marriage and a movement to repeal the abortion ban. He shares his family's daily life while he worked at Slack Dublin, noting the company's growth and shift to a sales-focused culture. James reflects on his own career challenges, including hiring a career coach. He emphasizes the importance of people in both his professional and personal life, cherishing the connections made during his time in Ireland.00:00 Introduction: An Irish Goodbye00:19 Social changes in Ireland01:26 Reflections on religion and society02:48 Brexit and its impact on Ireland03:28 Personal and professional growth03:56 Slack Dublin: growth and transition05:27 It's the people08:43 Moving forward: new role and reflections This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Values of the Slack Product: Part 2In this episode, James Sherrett tells the story of Slack's journey in launching the Enterprise Grid product. Through a metaphor inspired by Lego platform sheets, Stewart Butterfield, Slack's co-founder, envisioned connecting multiple Slack workspaces to form an interlinked network. The episode explores the motivations behind this new product, including demands from existing and prospective large customers as well as Slack's own growth needs. Sherrett highlights the challenges and changes faced by Slack in appealing to 'BigCos,' such as increased security features and compliance requirements. This shift involved balancing Slack’s original values with those required by large enterprises, ultimately transforming Slack's product offerings and positioning it for substantial growth.00:00 Introduction to Slack's Enterprise Journey00:29 The metaphor of Enterprise Grid01:32 Challenges with large customers05:43 Prospective customer needs08:33 Slack's needs and market strategy10:22 The launch of Enterprise Grid11:54 Values and technological shifts14:05 Holistic vs. Prescriptive technologies17:12 The impact of Enterprise Grid on Slack18:53 Conclusion and future outlook This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Exploring the Values of the Slack Product: Part OneIn this episode, James Sherrett delves into the starting values of the Slack product and how those values evolved over time. With personal anecdotes and a model of technology from Ursula Franklin's The real World of Technology, James focuses on 3 values of "the system of Slack": default to trust and openness, a shared reality and compassion through service. How were each of these connected to Slack's design and reflecting the original team’s work philosophy? Then, how did they change over time?00:00 Introduction: The Values of Slack00:59 The shift to product values02:01 Personal reflections and Dublin insights03:55 Technology and its broader context07:40 The System of Slack09:20 3 values of the System of Slack09:49 Default to trust and openness12:35 A shared reality through channels15:07 Delivering compassion through service19:50 Adapting to larger customers21:10 What to expect in part 2 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

A True Irish Coffee Experience — Reviving an Authentic TraditionIn this episode, James Sherrett recounts his first Christmas in Ireland, some family traditions and a memorable encounter with Irish neighbors. After being invited for a holiday drink, we discovered the true essence of Irish coffee, a far cry from the mediocre versions previously known. We leave with a deliciously rich and savory homemade Irish coffee recipe. We repatriate the recipe to Canada and it becomes a tradition for family and friends. The episode concludes with the Irish coffee recipe and a cautionary note on moderation.00:00 Introduction: A Irish Irish coffee tale00:18 Settling into Irish life01:20 Meeting the beighbors03:35 A memorable afternoon04:43 The perfect Irish Irish coffee recipe07:07 Serving recommendations This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Building Slack's Success in Europe: Leadership Transition & ExpansionJames Sherrett recounts his experience establishing Slack's EMEA offices in Dublin and London. He reflects on his journey, which included recruiting and training his team, finding new office spaces, and scaling the business from 30 to 120 employees. Sherrett focuses on the leadership transition, detailing his meetings with prospective candidates, especially Johan Butting, who eventually succeeded him. And then what?00:13 Opening Slack's EMEA offices01:28 Meeting potential new leaders03:24 Always building, building, building the team04:07 Rooftop restaurants08:12 New Dublin office acreage10:25 Official Search for a New Leader12:48 Conclusion: Next Steps and Irish Coffees This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Building Slack London: Growth, Challenges, and Lessons LearnedIn this episode, James Sherrett narrates the story of establishing Slack's London office, detailing the company's strategic growth and the beginning of its Customer Success practices. Starting with the first hire, Rav Daliwhal, James recounts the early challenges of locating suitable London office space and adapting to the emerging field of customer success. The narrative explores the evolving complexity of Slack's sales teams, reflecting on the company's gentrification and organizational changes. Significant customer acquisitions, office expansions, and the shift from a startup mentality to a structured enterprise come up. James also shares personal insights about the mistakes he made during this growth phase, shedding light on changes in hiring practices and the balancing act between retaining Slack's unique culture and striving for growth. The episode concludes with a teaser on prospecting candidates and further developments in Dublin.00:00 Introduction: The Slack London Story Begins00:25 Meeting Rav Dal: The Start of Customer Success02:21 Establishing Slack London: Challenges and Growth02:51 The WeWork Experience: Pros and Cons04:13 Building the Team: New Hires and Roles04:58 Growing Pains: Transitioning to a Sales Team06:25 Major Clients and Customization08:37 Office Expansion: Moving to Ying House12:50 Reflections on Leadership and Hiring Mistakes21:58 Conclusion: Embracing Change and Growth This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Slack's European Expansion MissionJames Sherrett narrates the journey to various European cities, from Dublin to London, Paris, and beyond, to promote and expand Slack. He details the challenges and successes of targeting tech-forward organizations, adapting to the unique nuances of over 20 smaller markets, and overcoming skepticism towards new, US technology. Sherrett emphasizes the importance of talking with customers, shares anecdotes from his travels, highlights internal challenges with hiring, and discusses balancing work with family life. This episode captures some key moments of the mission to introduce Slack to Europe.00:23 Taking on the Mission: Spreading the Word About Slack01:43 Carving off European markets: challenges and opportunities02:33 Establishing a presence in London03:33 Customer Success stories: Sky News, Ocado, and more04:18 Hiring challenges and cultural insights04:49 Meeting GE in Cardiff06:20 TechCracker conference at Stirling Castle in Scotland13:44 Struggling with work and family during travel14:59 Reflections and personal sacrifices16:22 Conclusion: the shared mission This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Teenage Years of Slack and Finding a Sales LeaderIn this episode, James Sherrett narrates the journey of Slack in its formative years, focusing on the challenge of hiring a VP of Sales. As the company moved beyond its development-driven roots, it realized the need for an experienced leader who could steer the Sales strategy. Despite internal skepticism about Sales, the team embarked on a rigorous interview process, eventually landing on a top 1 candidate, Bob Frati. Bob's readiness to learn and adapt made him a strong fit, and marked a key turning point in Slack's strategy to scale up its Sales functions. This episode is full of the growing pains and excitement of evolving from a startup to a larger commercial entity.00:23 The Challenge of Hiring a New Boss01:46 Internal Struggles and Realizations06:12 The Search for the Right Candidate10:19 Interviewing Bob: A Standout Candidate14:47 Bob's Impact and the Future of Slack15:47 Conclusion: Expanding Horizons This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Growing Pains at Slack: Embracing Sales and Scaling UpJames Sherrett narrates Slack's realization we needed to grow up. But what did that mean? And how did we scale up our sales organization to match the increasingly complex demands of larger customers without losing what made the experience excellent for customers. Sherrett recalls some of challenges faced, solutions implemented, and pivotal decisions made. Key moments include adding specialized roles like solution engineers and customer success managers, then evolving our internal identity during an offsite meeting.00:17 Facing the need to grow up03:22 Preparing for change: the latest offsite04:29 Defining a team identity07:28 Competency traps and customer matching12:03 Sales Math: Oh, look, customer expectations13:49 Becoming Sales finally, an anti-climax15:34 Conclusion: Hello world This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

A Dublin Office Halloween: Slack's Journey with Stewart ButterfieldSlack's had its Dublin office, the first outside the Pacific Time zone. Now Slack CEO, Stewart Butterfield, came calling. Also: Hallowe'en. Also: Callowe'en. We reflect on Stewart's growing role and influence both within and outside Slack, including the 'cult of personality' surrounding him. The story finishes by contrasting Slack's values with those of Salesforce after the acquisition.00:00 Introduction: A Slack Story by James Sherrett00:48 Halloween in Dublin: riding the leprechaun01:25 Preparing for Stewart's visit03:04 All Hands meeting from Dublin06:13 Changes happening for Stewart and Slack's culture08:33 The One Mind theory of startups11:05 Style and substance and sprezzatura13:40 The Salesforce acquisition and cultural mismatch This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Building Slack Dublin from PeopleJames Sherrett recounts his experience of building Slack's team in Dublin from three to 62 employees over 27 months. The journey involved adapting recruitment strategies, localizing the hiring process, and selling Slack to prospective employees alongside customers.Sherrett highlights the initial successes and subsequent challenges in hiring the right talent, including notable hires like Alia Lamadaar, Paul Murray, and others. He reflects on some of the lessons learned and the unique qualities that made Slack's Dublin team successful. He touches on local recruitment methods, including challengine recruiters and seeking employee referrals, that eventually led to a promising Slack Dublin.00:00 Introduction: A Slack Story by James Sherrett00:18 Building the team: from 3 to 62 in Dublin00:53 The transposed hiring process: screening and interviewing01:52 Selling Slack to candidates04:30 Challenges in recruitment05:56 Adapting Slack to Ireland08:14 Success stories: small wins and first 5 key hires11:48 A little from column A, a little from column B12:11 Walking and talking: the Ciaran Chaney experience14:36 Conclusion: Slack is made of people This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

0:38 — The Official Photo and Slack launch event at Trinity College Dublin1:22 — Meeting the Irish Prime Minister, cultural observations2:32 — Media questions: jobs, hiring, and Ireland’s expectations3:01 — The importance of PR and community in Slack’s early success3:30 — Expanding the story for a broader audience, tech status in Europe4:52 — Slack’s recognition in different cities and challenges in Europe5:24 — What is Slack? Shifting the story to employment and growth6:02 — Tech industry size in Dublin, yet battling local skepticism6:49 — Outline of Slack’s European expansion strategy7:16 — Building teams, market groupings, and EMEA offices7:43 — Lessons in global market sizing and Europe’s complexity8:10 — The US market advantage, cultural unity9:02 — Pockets of Slack adoption in Sweden, Lithuania, Russia, UK9:23 — Challenges in less receptive European markets10:13 — Meeting LVMH in Paris, cultural nuances10:49 — Berlin IT conference: demos, user engagement, and presentations12:55 — Frankfurt: learning from German family businesses (Tand)13:09 — Selling to skeptics, Bosch, Volkswagen, and progressivism13:31 — Flashbacks to early Slack days, present challenges13:52 — Helping customers build internal cases for Slack14:12 — Presenting to a secretive client in London14:33 — The Sovereign Military Order of Malta: unique client, no deal14:56 — Realization: being used for a “bake off,” lessons learned15:22 — Lessons: pre-qualify opportunities, know your customer16:24 — Hostility to new software, communication concerns16:47 — Relational tactics: comparing Slack to texting and news alerts17:08 — The Maya principle: recalibrating “most advanced yet acceptable”17:30 — Flailing, finding footing, and sales challenges in EMEA18:09 — Next challenges: hiring expertise to change the leaderboard18:30 — Bonus story: interviewing Ciaran Cheney, Slack’s future office manager19:13 — Ciaran’s hiring, celebration at The Long Hall20:09 — Looking ahead: hiring Irish hybrids, finding and addressing biases This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Introduction: Moving to Dublin, settling in, and the challenge of starting over.00:30 — Adjusting to a new city: Finding housing, coffee shops, and routines.00:54 — Working from the Guinness Storehouse, feeling like a traveler.01:21 — Balancing old and new: Letting go of Vancouver responsibilities, focusing on Dublin.01:41 — "Culture Carrier" role: What it means and why it matters to a new office.02:51 — The many hats of Culture Carriers.03:16 — Translating company culture: Connecting Slack’s values to Dublin’s context.03:44 — Introducing Hanni: Her energy, background, and partnership.04:33 — The Fridge Incident: The struggle to get a fridge for the new office.06:11 — Lessons from the fridge: Teamwork, regret, and learning to see others’ needs.08:19 — Building a Dublin office: Weekly leadership meetings, office culture, and hiring.09:43 — The challenge of newness: Overwhelm, adaptation, and family life in Dublin.10:11 — Appreciating colleagues: Hanni’s initiative and the value of partnership.10:32 — Creating local culture: Adapting Slack’s values, painting the office, and working to create a sense of belonging.11:06 — Don't call it a remit: Balancing duties with whatever it takes to succeed.12:16 — Embracing the "yes, and" role: Flexibility, learning, and holding onto essentials.13:21 — Up next: Preparing to launch Slack in Europe. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Boom Times, Not Boom TimesArriving in Ireland, first impressions, and the legacy of the Celtic Tiger.0:31 — The Celtic Tiger era: Irish attitudes toward the boom years and the real estate bust.0:59 — The aftermath: Bank bailouts, national debt, and the business context we found as we moved to Ireland to open Slack’s AMEA HQ.1:22 — Learning Irish business culture: Distrust of wealth and the influence of Catholic history.1:55 — Money and Irish identity: Tension between enthusiasm for success and fear of collapse.2:18 — Reading up: Michael Lewis on the Celtic Tiger and the mythic importance of land ownership.2:42 — The Irish play the field: Land, history, and the new tech-driven boom.3:04 — The new boom: US tech companies, Slack’s role, and Irish identity.3:37 — Rich and poor: Tax avoidance, emigration, and the evolving Irish diaspora.4:30 — A changed Ireland: Return migration, new opportunities, and a maturing economy.5:25 — Dublin’s transformation: Housing shortages, digital nomads, and Slack’s diverse team.6:24 — Irish hidden culture: Home counties, accents, and university traditions.6:54 — Upward mobility: Dublin’s draw, real business, and the flow of venture capital.7:38 — Tech’s impact: 10–20% of Dublin’s workforce in tech, joining a new world.8:02 — Real estate stories: House prices before, during, and after the crash.8:48 — Lingering effects: The Celtic Tiger’s hangover, corporate and personal taxes.9:14 — Taxes in Ireland: High rates, deductions at source, and a sense of shared burden. An automated tax system: No returns for most, a mix of relief and helplessness.10:04 — Playground conversations: Meeting locals, signs of a new boom.11:45 — Exploring Dublin: Buses, the zoo, and the city’s layered history.12:19 — Glimpses of hardship: North side poverty, abandoned buildings, and urban contrasts.12:44 — Dublin in transition: The city’s past and future, setting up the next story.13:20 — Closing: Thank you and a teaser for the next episode. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Stone Upon Stone[0:00] Opening Slack's Dublin offices at the Guinness Storehouse.[0:21] Reflections on the unique character of The Liberties neighborhood, its working-class history, and vibrant street life.[0:59] Descriptions of the old Guinness warehouses, cobbled streets, and its transformation into a startup hub.[1:45] Stories about local shops, markets, and the quirky details of daily life in Dublin.[3:28] Discovery of a poem, "Stone upon stone upon fallen stone," stenciled on a high wall, and its connection to the area's history.[5:23] Personal experiences navigating Dublin's winding streets, learning the city by foot and bike, and the challenges of orientation.[6:22] Observations on the Dublin contrast between The Liberties and the more tourist-oriented city center.[7:13] Family adventures: playgrounds, bus rides, the Dublin Zoo, and the Viking Splash tour.[8:16] Insights into Irish culture, including local naming conventions and the spirit of the city.[8:56] The journey of settling into a new home, embracing both the familiar and the unknown.Next episode: Learning about Ireland, starting in Dublin, exploring its history—some well remembered, some purposefully forgotten. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Leaving for Dublin00:00 — Introduction: The Big Move, a new position in Dublin, the decision to move, and the challenges ahead.00:36 — Becoming the First and facing the unknownThe family prepares to be the first to make this kind of move at Slack, with new responsibilities and uncertainties.01:03 — Family sacrificesSaying yes to big changes, including my wife leaving her job and our son leaving his routine.01:29 — Packing up and letting goLeaving our long-time home, selling possessions, and preparing for a new life.01:56 — Logistics and unanswered questionsManaging the move, selling items, and dealing with the unknowns about returning and succeeding in Dublin.02:51 — Arriving in Ireland: new beginningsLanding in Dublin, adapting to new routines, and the importance of small comforts like the family stroller / buggy.04:12 — Farewells and reflectionsSaying goodbye to colleagues, the emotions of leaving, and the support from the Slack YVR team.05:47 — Acknowledging inequalityReflecting on the sacrifices made, the challenges of balancing careers, and the realities of modern work and family life.07:18 — Looking back, moving forwardConsidering the decision in hindsight, the risks involved, and the desire to live and work internationally.08:22 — Striving for balanceSecuring work permits for both, making decisions together, and aiming for fairness in the family.09:05 — On ongoing journeyRecognizing the ongoing imbalance, the hope to rebalance in the future, and the broader context of gender roles.09:49 — Up nextA preview of what’s next: opening Slack’s Dublin office, finding poetry in the city, and gratitude for the journey. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Eee Mee Yah and Slack's International HQEarly mornings in Vancouver: Preparing for European calls and the excitement of working with international teams. (0:00)The value of research: Personalizing client interactions and surprising customers with tailored insights. (0:37)Slack’s global ambitions: The growing demand from Europe and the decision to expand internationally. (2:43)The Dublin scouting trip: First impressions of the city, meetings with IDA Ireland, local agencies, and exploring potential office locations. (3:32)Learning the language of international business: Acronyms, market structures, and the unique culture of Dublin’s tech scene. (6:50)Why Dublin? Tax advantages, a strong talent pool, and a welcoming environment for tech companies. (9:01)Comparing European options: Weighing Dublin against other cities like Amsterdam, London, Galway, and Cork. (10:24)Deciding on Dublin: The team’s growing conviction and the practicalities of relocating. (11:32)Exploring neighborhoods: Searching for a home, local amenities, and adapting to Dublin’s lifestyle. (12:54)Observing Dublin’s transformation: The city’s evolving identity, social divides, and the blend of tradition and modernity. (14:07)The family’s journey: Preparing for the move, embracing change, and reflecting on the adventure ahead. (16:07)Conclusion: Reflections on the move and what comes next. (16:44) This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

How Slack Built its Culture: Part 3In this episode, James Sherrett shares the inside story of how Slack’s culture was built and lived, focusing on the daily practices, values, and rituals that shaped the company.Timestamps & Topics:[0:00] IntroductionOverview of Slack’s culture journey, the four attributes, and six core values.[1:37] What is Culture, Really?Exploring the meaning of culture, referencing The Culture Code by Daniel Coyle.[3:16] Slack’s Mission: SPPThe origin and impact of “Simpler, more Pleasant, and more Productive” on Slack’s daily work.[4:39] Never Waste a Crisis[4:39] The 2015 security breach, how Slack responded, and the values that guided the team.[7:53] The Power of Affirmations[7:53] The story behind the “What good shall I do this day?” sign and how small rituals reinforced culture.[9:56] Rethinking Sales Compensation[9:56] The debate over how to pay salespeople, insights from Drive by Dan Pink, and the evolution of Slack’s approach.[13:07] Calle-oween: A Unique Ritual[13:07] The tradition of dressing as CTO Cal Henderson and celebrating consistency and dedication.[15:13] Closing Thoughts[15:13] Reflections on culture, rituals, and the journey.Notable Quotes & References:• “Culture is a set of living relationships working toward a shared goal. It’s not something you are, it’s something you do.” — Daniel Coyle, The Culture Code• “What good shall I do this day?” — Benjamin Franklin• Insights on motivation and autonomy, mastery and purpose from Drive by Dan Pink.Takeaways:• Culture is more than words on a wall—it’s how values show up in everyday decisions, crises, and celebrations.• Rituals, stories, and even small signs can reinforce shared values and purpose.• Adapting to challenges and being willing to question industry norms are key to building a resilient, authentic culture. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

How Slack Built Its Culture: Part Two - Eating the GoatThis episode, 'Eating the Goat,' explores how Slack recognized and addressed rapid hiring issues and built a strong organizational culture. Slack's CEO Stewart Butterfield used the analogy of a snake eating a goat to describe the current state Slack found itself in. To solve it's problem, Slack developed its Six Slack Values — craftsmanship, empathy, thriving, courtesy, playfulness, solidarity — and created stories and onboarding processes to embed these values in daily work. Then Slack made onboarding into a force multiplier for everyone who joined in Slack's growth.00:00 Introduction: A Slack Story by James Sheret00:24 The Goat Analogy: Digesting Growth Challenges04:51 Codifying Slack's Culture: The Four Attributes05:26 Introducing the Six Slack Values08:40 Craftsmanship: Painting the Back of the Drawer10:09 Empathy and Courtesy: Understanding and Helping Customers14:11 Onboarding as a Force Multiplier17:30 Conclusion: Reflecting on Slack's Cultural Evolution This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Inside Slack: Defining Culture with Four AttributesIn this episode, James Sherrett shares how Slack began to define its company culture by establishing Four Slack Attributes. Learn about the challenges faced due to rapid growth and how founding personalities like Stewart Butterfield impacted the evolving culture. Sherrett recounts the creation of the four Slack attributes — smart, humble, hardworking, and collaborative — and reflects on their role in guiding (or not guiding) team behaviour. Despite being a solid step ahead, the Four Slack Attributes faced limitations and required interpretation for new members.00:00 Introduction: The Slack Story Begins00:07 Defining Slack's Culture: The Four Attributes01:14 Unveiling the Four Slack Attributes02:14 Smart: The First Attribute03:11 Humble: The Second Attribute04:14 Hardworking: The Third Attribute05:08 Collaborative: The Fourth Attribute06:18 Reflecting on the Four Attributes07:28 The Need for Evolution This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Building a High-Performance Culture at SlackHow did we start to establish a high-performance work culture at Slack? It starts by examining the company's hiring philosophy, rooted in the high expectation of doing the best work of one's life. This expectation acted as a filtering mechanism to identify optimistic and proactive candidates who embraced challenges. Dig into the internal processes and principles of the accounts team, such as decision-making using a 'trinity' of questions and the 'search first' mentality, to maintain efficiency and autonomous problem-solving. These cultural norms fostered trust, transparency, and a commitment to excellence within the team. The episode concludes with a preview of an upcoming discussion on the foundational values that underpin Slack's culture.00:00 Introduction: A Slack Story by James Sherrett00:20 The Slack Interview Experience01:01 Setting High Expectations at Slack01:46 The Challenge of Doing Your Best Work04:39 Empowering Decision Making with the Trinity07:21 The Power of 'Search First'10:58 What might a Slack culture look like? This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Slack's Rise: From Coffee Shops to Celebrity EndorsementsJames Sherrett recounts the thrilling journey of Slack's growth and wider adoption, from everyday encounters at coffee shops to attracting celebrity investors like Jared Leto and Snoop Dogg. He discusses the company's transition into larger office spaces in San Francisco and Vancouver and touches on the cultural evolution within Slack. The episode provides a glimpse into the remarkable milestones and the increasing recognition that marked Slack's journey to becoming a billion-dollar unicorn.00:00 Introduction: Slack's Rise to Fame00:32 Slack in the Wild: Real-World Encounters01:43 Celebrity Endorsements and Investments02:41 New Office Spaces: Growth and Expansion03:59 Defining Slack's Culture and Future04:26 Conclusion: Building the Future of Slack This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Slack's Billion Dollar Journey: Inside the Fundraising MilestoneIn this narrative by James Sherrett, the story unfolds about Slack achieving a billion-dollar valuation. It covers the inner workings of living through a significant fundraising announcement and the emotions and routines within the Slack team during this period.Sherrett reflects on the sudden shift in their valuation and what it represented, accompanied by media coverage and internal reactions. The script delves into the dynamics of Slack’s growth, highlighting the importance of their PR strategy, their compelling story, and the contributions of their leadership and teams. How does it feel to become a unicorn? 00:00 Introduction: A Day in the Life at Slack01:01 The Big News: Fundraising Announcement02:23 Reflecting on the Billion Dollar Valuation04:29 Understanding the Impact of Fundraising08:26 The Role of PR in Slack's Success11:38 Conclusion: Slack's Journey to Fame This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Meet the New New Boss: A.J.This episode, narrated by James Sherrett, focuses on the challenges of adapting to new leadership. James recounts receiving an unexpected call from his boss, Allen Shim, Slack's CFO, informing him of his new boss, AJ. He shares his initial apprehensions, the strategic decision-making process, and the dynamics of working closely with AJ. Through detailed notes and reflections, James highlights the complexities of balancing immediate tasks with future planning in a rapidly growing startup. The narrative underscores the importance of adaptability, trust, and forward-thinking in thriving within a transformative company environment, and how these attributes did not come quickly or easily to James.00:00 Introduction: A Slack Story by James Sherrett00:21 The Unexpected Call01:25 Meeting the New New Boss, AJ02:05 Navigating Uncertainty03:31 Reflecting on the Changes05:10 Allen's Strategy and AJ's Role07:10 Building the Team07:53 AJ's Visit to Vancouver09:08 Adapting to Change12:34 Future Vision and Strategy15:12 Conclusion: Lessons Maybe Learned This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

The First Five: How Slack Hired Its Initial Sales TeamIn this episode, James Sherrett narrates the story of how Slack hired its first five salespeople. He outlines the challenges of hiring salespeople without prior experience, the development of a candidate evaluation process inspired by Daniel Kahneman's work, and the creation of effective job descriptions. He also details a 5-step hiring process including writing assignments, presentations, interviews, and reference checks. Sherrett shares insights into the traits they looked for in candidates and the success of the hires, emphasizing their impact on Slack's growth. Finally, he reflects on the achievements and career advancements of these 5 foundational team members.00:00 Introduction: The Slack Hiring Journey00:21 Facing the Challenge: Hiring Salespeople00:53 Creating an Evaluation Process01:46 Inspired by Kahneman: Faceted Evaluation03:28 Crafting the Perfect Job Description06:19 The Application Process: Writing Assignments10:48 Evaluating Written Assignments13:54 Sales Presentations: Zoom Demos15:46 In-Person Interviews: The Final Step22:46 The First Five Hires26:34 Conclusion: Reflecting on the Journey27:19 Next Up: Selling to Enterprises This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Navigating Rapid Growth at Slack: Customer Segmentation and the Path to Scaling upIn this episode, James Sherrett covers the whirlwind journey of Slack's growth from its inception to hitting $10-million in annual recurring revenue in 8 months. He highlights the overwhelming yet exhilarating experience of managing the rapidly increasing customer base. Then how Slack identified three key customer segments—self-service users, small and medium-sized businesses, and enterprise. James previews his third role as Slack’s first Sales Manager and the key question he faced: who to hire to drive the company's explosive growth from $10-million to $100-million?00:00 Introduction: A Slack Story by James Sherrett00:24 The Overwhelming Growth of Slack01:38 Hiring Help and Customer Segments03:02 Understanding Our Customers03:59 Identifying Customer Types06:42 The Barbell Distribution08:06 Preparing for Future Growth08:35 Transition to Sales Manager10:00 Up next: Hiring Good Hybrids This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Unveiling Easter Eggs in Slack: A Journey of Playfulness and ProductivityIn this episode, James Sherrett shares the playful and intricate details behind the design of Slack, highlighting how the software incorporates game-like features known as Easter eggs. The narrative explores various hidden gems like custom loading messages, the self-loathing web socket error message, the story behind the introduction of the Shruggy emoticon, and the inventive use of slash commands.Additional touches include the reordering of emojis for a positive user experience, the surprise animations hidden in the preferences section, and the user-friendly Slack bot. The episode emphasizes how these playful elements make the work communication platform engaging and delightful for users.00:00 Introduction: The Game of Work01:31 Easter Eggs in Slack: An Overview01:44 Custom Loading Messages: Making Waiting Fun03:10 Web Socket Woes: Connection Troubles04:50 Slash Commands: Hidden Treasures06:58 Emoji Decisions: Injecting Fun into Work08:45 Preferences Menu: Hidden Features10:08 Slack Bot: Your Friendly Guide11:04 Conclusion: Share Your Favorite Easter Eggs This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Creating Slack's Launch Video: Behind the ScenesJames Sherrett narrates the story of Slack's launch video, produced by Sandwich Video in 2014. He explains the significance of having a Sandwich video for a tech startup, detailing the video's production, the script collaboration between Slack's team and Sandwich, and the quest for a fitting title. The final title, 'So Yeah, We Tried Slack,' emerged from a key line in the video. Sherrett also mentions a sequel video created during the COVID-19 pandemic and teases future content on Slack's Easter eggs and unique features.00:00 Introduction: The Quest for a Sandwich Video01:21 The Making of the Video01:52 The Title Dilemma02:37 The Final Decision04:04 Aftermath and Reflections04:37 Easter Eggs in Slack This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Slack's Journey to Fair Billing and Effective Pricing StrategiesBy 2014, Slack saw consistent weekly growth and recognized that once teams started using the platform, they rarely stopped. There were two main growth drivers – acquiring new customers and expanding in existing customers – and two main tensions Slack faced, particularly the hybrid use of multiple communication tools.To address these tensions, Slack adopted three key pricing principles: simplicity for new customers, fairness for existing ones, and speed for deployment. Specific tactics like starting with a high pricing point, avoiding unlimited user deals, and offering credits instead of discounts were employed. The highlight is the fair billing policy, which ensured users were only charged for active usage, boosting customer trust and simplifying billing processes.The story winds up with a nod to Slack's long-term approach to customer satisfaction and its impact on their sustained business growth.00:00 Introduction: A Slack Story by James Sherrett00:22 Understanding Slack's Growth Levers01:12 New Customers: The First Growth Source01:58 Expansion of Existing Customers03:32 Tensions in Slack's Growth Model05:50 Principles of Slack's Pricing Strategy08:21 Tactics for Implementing Pricing Principles15:49 The Fair Billing Policy Origin Story21:40 Conclusion: Reflecting on Slack's Journey and Lazy Computer Programmers This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Slack's Early Days: Sonoma Offsite ReflectionsIn this episode, James Sherrett recounts his first offsite experience with Slack in Sonoma on May 15th, 2014. The narrative captures the early, intimate scale of Slack's global workforce of around 30 employees, the significance of in-person interactions in a remote-first company, and the excitement surrounding their burgeoning product success. Sherrett shares his initial thoughts and questions about offsites, his reflections on meeting his new boss Allen Shim, and the profound realizations about Slack's potential and future. Highlights include candid moments with colleagues and pioneering discussions on product and customer interaction, illustrating the blend of meticulous work and imaginary thinking that characterized Slack's early growth.00:00 Introduction: A Slack Story by James Sherrett00:27 First Offsite Experience in Sonoma02:26 Meeting the New Boss: Allen05:43 Getting to Know the Team07:50 Offsite Activities and Reflections10:11 The Future of Slack: Aspirations and Challenges12:45 Conclusion: Embracing Change and Change and Change This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Navigating Sales in Slack: Early Deals and Hard-Learned LessonsJames Sherrett recounts his experiences of closing early sales deals at Slack without a traditional sales team. He describes the significance of celebrating wins through dedicated Slack channels and shares a memorable story about negotiating with Sauce Labs, a customer demanding a discount. The narrative highlights the importance of understanding customer needs and being prepared for tough negotiations. Sherrett explains how these early experiences and the detailed pricing proposals were pivotal in refining Slack's approach to sales and customer success.00:00 Introduction: A Slack Story by James Sherrett00:19 The First Deal: Celebrating Wins01:16 Creating the #accounts Channel03:27 Memorable #accounts Post: Sauce Labs05:09 The Cannon09:32 Crafting the Perfect Pricing Proposal18:14 Conclusion: Lessons Learned19:28 Teaser: Up Next - Offsite in Sonoma This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

The Twitter Game: Building Slack's Wall of LoveThis episode explores how Slack effectively used Twitter to connect with its tech-savvy audience and amplify customer feedback. It details the creation and evolution of Slack's 'Wall of Love,' a curated collection of positive tweets that addressed customer objections and showcased unsolicited endorsements. The narration emphasizes the significance of customer engagement on Twitter and describes internal processes designed to maximize the surface area of the company to customer feedback.00:00 Introduction: A Slack Story by James Sherrett00:22 The Early Days: Twitter as a Key Platform01:46 Playing the Twitter Game05:23 Creating the Wall of Love07:29 Managing and Expanding the Wall of Love11:06 Maximizing Customer Feedback14:30 Conclusion: The Importance of Customer Interaction This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Launching Paid Slack: The Journey from Free to PaidIn this episode, James Sherrett shares the story of how Slack transitioned from a free to a paid product. From the early planning stages, the company knew its business model would be a B2B SaaS offering. The script details the use of credits to ease the transition for customers, and the data-driven approach that helped identify key patterns in user growth and retention. As Slack prepared for its February 12, 2014 launch, the team used customer feedback, analytics, and strategic PR to ensure a successful rollout. The episode also touches on the company's early struggles and the pivotal role of customer stories in achieving long-term success.00:00 Introduction: Launching Paid Slack00:23 Defining the Business Model00:51 Customer Engagement and Feedback02:41 Analyzing User Data04:08 Preparing for Launch10:14 The Launch Day13:17 Post-Launch Reflections18:29 Continued Growth and Customer Relations This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

The Slack Socks Saga: A Quirky Marketing SuccessIn this episode, James Sherrett narrates the fascinating journey of how Slack created custom socks as a unique marketing tool. Starting with a small budget, the team decided to use socks featuring their tartan design as company swag. The process wasn't easy and included a 99-email thread just to finalize designs.Despite initial challenges, the socks became immensely popular, eventually leading to orders of up to 500,000 pairs. The socks not only contributed to brand identity but also symbolized the quirky originality and growing pains of Slack as it transitioned from a startup to a large business. The narrative concludes with reflections on how the company's unique identity evolved and adapted as it grew.00:00 The Slack Socks Story Begins00:22 Why Socks? The Marketing Strategy02:25 Design Challenges and Email Correspondence05:50 The Popularity of Slack Socks06:56 Evolving Designs and Internal Impact10:20 Reflections on Growth and Change13:02 Conclusion and Transition to Paid Slack This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Saying No Nicely: A Slack Story by James SherrettIn this episode, James Sherrett starts at Slack in 2014 as full-time Director, Accounts. He discusses the evolving roles and responsibilities in a small startup environment, focusing on customer interactions, providing demos, and collecting feedback.A key theme is the philosophy of 'saying no nicely,' both to customers and in shaping product strategies. James explores different ways to decline requests respectfully and strategically, the impact of this approach on customer satisfaction, and the overall business operations. Additionally, he touches upon the growth of Slack, its core functionalities, and how it became a pivotal tool for digital communication and teamwork.00:00 Introduction: Starting in Accounts at Slack01:33 Customer Interactions: Helping and Selling02:24 The Art of Saying No Nicely03:01 Examples of Saying No Nicely04:50 Learning from Customer Feedback06:37 The Philosophy of Saying No Nicely12:24 Slack's Core Functionality in 201414:39 The Complexity of Messaging15:48 Being a Guide and Guard16:48 Saying No Nicely: A Continued Practice17:36 Conclusion: Focus Drives Results18:03 Up Next: Slack Socks This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Transition from Marketing to Accounts at SlackA quick episode to mark the transition of the story from Part 1 to Part 2. A thank you for the audience's support and feedback. A recap of the topics covered so far. A sneak peek into what's coming next, including launching Slack's paid product and creating the Slack Wall of Love. If you're reading this you likely already know about the accompanying podcast.00:00 Introduction to the Slack Story00:23 Transition to Part Two00:40 Preview of Part Two01:05 Three Things01:36 Recap of Part One02:40 Podcast Information03:07 Feedback Request03:38 Okay, onwards This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

Please sit next to the moneyIn this episode, James Sherrett narrates his tumultuous journey at Slack, starting as a consultant in June 2013, navigating through periods of high demand, strategic pivots, and personal struggles. Despite initial setbacks, including a retracted job offer, James continued to show up for work. His persistence and growing alignment with the team ultimately led to his official hiring as the Director, Accounts at the end of 2013. James shares insightful anecdotes about customer engagement, internal teamwork, and the evolving dynamics of startup culture, providing a behind-the-scenes look at Slack's early days. James' wife Monique also makes an appearance to offer her perspective.00:00 Introduction00:28 Early Days at Slack: Joining the Team01:32 Marketing and Customer Engagement03:12 Scaling Up: Handling Increased Demand03:58 The Polite Struggle for Control07:12 A Turning Point: December 201311:12 Monique Shares her Perspective22:04 Final Decision: Joining as Director, Accounts This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

The First 1000 Slack Invites: Insights and ObservationsIn this episode, James Sherrett shares the insights drawn from the first 1,000 Slack invites, from September, 2013. He shares 16 key observations about user behaviour and feedback that contributed to Slack's development and positioning. Despite early challenges, these initial signals of success helped shape Slack's journey to becoming a billion-dollar company. Toward the end, we cover hindsight bias and retaining the context of those formative days. The episode provides a unique glimpse into the embryonic stages of Slack's growth.00:00 Introduction: A Slack Story by James Sherrett00:28 The First 1000 Slack Invites: Initial Observations00:42 Context and Early Success02:09 Inviting Teams and Gathering Feedback03:35 Key Observations from the First 1,000 Invites09:34 Reflecting on the Observations10:26 The Journey of Slack: From Zero to Success11:39 Conclusion: The Reality of Startup Success This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com

A Foundational Slack Story: Craftsmanship and CultureIn this episode, James Sherrett recounts a defining story shared by Stewart Butterfield, co-founder of Slack, about learning the importance of reputation and pride in good work at an early age. The narrative underscores the value of conscientiousness and accountability, pivotal to Slack's company culture. Stewart’s father taught him that every job bears his name, a lesson that extended into Slack's ethos. The episode explores how this principle was embedded into Slack's cultural fabric as it evolved from a small team into a larger enterprise. Next, the show will delve into early observations from Slack's first 1000 invites.00:00 Introduction: A Slack Story by James Sheret00:12 Defining Slack Culture Through Stories00:20 Stewart's Childhood Lesson on Reputation01:13 The Cord of Wood Challenge03:27 The Importance of Craftsmanship at Slack04:26 The Impact of Stewart's Story on Slack's Work Ethic05:18 Reflecting on Slack's Early Days05:49 Conclusion: Embracing Accountability and Growth06:21 Up Next: Insights from the First 1000 Slack Invites This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.slackstory.com