Cracking Outbound

Harry Monkhouse runs global outbound at LastPass, where most people still know them as a password manager. But with 35M+ users and a brand-new B2B product, his team is building a pipeline from scratch, without a strong outbound history to lean on.In this episode, Harry breaks down how he’s using trigger-based plays, website signals, and old-school cold calls to drive meetings. We talk about why he left AE life to return to SDR leadership, what he learned from 6sense and Terminus, and why AI agents will change the game way sooner than most people think.If you care about pipeline, hiring, or where outbound is headed, this one’s worth your time.In this episode, you’ll learn:Why AI agents might replace parts of the BDR role in 3 years and what to do about it nowHow to run outbound with a massive B2C user base and minimal historical motionWhy the best reps and managers focus on trigger-based selling and consistent playbooksThings to listen for: (00:00) Introduction(01:19) Why outbound leaders should think more like operators(02:32) Lessons from working at 6sense and Terminus(04:58) Trigger-based outbound plays that still work in 2025(06:38) How stepping back into BDR leadership changed Harry’s career(09:13) The one skill Harry hires across every region(11:40) What AI is already doing well in outbound(13:25) How reps should think about AI agents in the near future(15:32) What selling looks like at a company with 35M B2C users(18:19) Turning personal users into a B2B pipeline(20:06) Using BDRs to drive customer expansion—not just net new(22:28) Coaching reps to work both expansion and outbound motions(24:41) The case for warmth: why outbound doesn’t have to be cold(25:57) Where Harry sees the next big outbound opportunity(27:44) Why most companies promote the wrong people into BDR leadership

Few people have reshaped an outbound culture quite like Jade Campbell.Now leading mid-market sales at Envoy, she’s spent the last six years building the company’s SDR function, shifting the org from inbound-heavy to outbound-driven, and managing one of the highest-output AE teams in SaaS.In this conversation with Todd Busler, Jade breaks down the frameworks she uses to create real accountability from pipeline-sourced goals to a live inbound router based on weekly performance. She explains how she motivates Gen Z reps without lowering the bar, how she changed behavior without overwhelming her team, and why most leaders underutilize deal reviews and dashboards.If you manage a team or are trying to drive more outbound motion in a tough market, this one’s worth your time.In this episode, you’ll learn:How Jade reworked Envoy’s outbound motion without overwhelming her teamWhy she built an accountability system tied to pipeline, not just activitiesWhat she does differently to earn rep trust and run a high-output teamThings to listen for: (00:00) Introduction(01:49) Jade’s background and role at Envoy(02:56) Evolving from visitor management to a workplace platform(03:13) Product marketing roots and how it shaped her sales approach(05:27) Fixing early outbound: blast emails and fuzzy ROEs(07:14) Why she shifted the team to a hybrid inbound-outbound model(09:07) Building early systems: where she started and what paid off(11:06) The enablement strategy behind multi-product selling(13:34) What she got right and wrong with outbound messaging(16:52) Meltwater’s intense sales culture and how it shaped her standards(18:53) Managing Gen Z reps with high expectations and real trust(21:29) The mistake new CROs make when they try to “fix” sales orgs(25:48) How she approaches performance management and tough calls(28:31) The weekly pipeline rule that decides who gets inbound(33:13) Building a true outbound culture at a formerly inbound org(36:52) Making sales culture fun without sacrificing performance(39:13) What keeps Jade motivated as a sales leader

Few people have observed as many go-to-market strategies as Liam Mulcahy.The Operating Partner at Kleiner Perkins has led sales at MongoDB, helped founders at Unusual Ventures find product-market fit, and has a front-row seat to what separates breakout companies from the rest.In this conversation with Todd Busler, he shares how top sellers should evaluate startups before joining, what founders often overlook when building their first sales team, and why making fast decisions beats perfect ones in early-stage growth. He also explains why technical fluency is quickly becoming the edge for modern sellers and what the best GTM teams all do to stay ahead in 2025.In this episode, you’ll learn:How to vet an early-stage company before taking the jobWhy founders’ beliefs about sales can make or break your careerWhat the next generation of elite sellers will look likeThings to listen for: (00:00) Introduction(02:21) Liam’s background and role at Kleiner Perkins(03:27) How to pick the right company to join(05:59) Evaluating founders’ views on sales(08:24) Why signed contracts are the new competitive moat(10:31) The changing definition of “early-stage” in the AI era(12:22) What real market pull looks like(15:13) How to tell if a founder believes in sales(24:27) What top early-stage GTM teams do differently(27:16) Decision velocity over decision perfection(33:21) Challenger selling vs. Value selling(39:44) The rise of technical sellers and the 2030 prediction

Outbound success doesn’t come from working harder; it comes from focusing smarter.In this conversation with Todd Busler, Scott Peyser discusses how they built systems that keep their operations running smoothly, from pipeline inspection frameworks to compensation levers to disciplined outbound cadences. After leading large teams at Dell, helping UiPath scale through its IPO, and shaping revenue operations at Clari, he’s now VP of Operations at CBTS. Scott shares what he’s learned building and refining outbound motions at every scale, from hypergrowth SaaS to billion-dollar service firms. He explains how clarity, consistency, and culture drive performance. Teams win when they inspect the pipeline with intention and commit real time to prospecting. The discipline is evident in the fundamentals, such as carving out time for outbound efforts, conducting weekly pipeline reviews, and focusing energy on areas with the most significant growth potential.In this episode, you’ll learn:How UiPath shifted its outbound motion to focus on expansion over new logosWhy consistent pipeline inspection drives healthier forecasting and growthWhat traits does Scott look for when hiring high-performing outbound repsThings to listen for: (00:00) Introduction(01:40) Lessons from UiPath’s hypergrowth and IPO experience(03:18) Building strong process discipline at EMC and Dell(04:12) The three pillars of effective outbound motion(05:41) Using compensation levers to drive net new pipeline(06:56) Forecasting pipeline and early pipeline metrics(08:00) CBTS’s shift to a services-first strategy(09:40) Creating repeatable revenue from expansion(13:23) Building trust and culture through guiding principles(15:51) Leading through tough quarters without losing the team(20:27) Hiring for intellect and drive in go-to-market roles(27:20) Why fast no is better than long maybes(29:23) Can SaaS reps sell services?

Many sales leaders come from quota-carrying roles. Terry Falk started as a corporate lawyer.Now VP of Software Sales at 8am, he oversees a team closing 400 new customers every month. He shares with Todd Busler how legal training shaped his approach to sales and why his time managing complex contracts helped him think clearly under pressure. He also breaks down the mistakes that slowed his early sales leadership, how he learned to build a pipeline without relying on inbound, and what running a high-velocity SMB motion looks like today.Listen in for a refreshingly honest take on getting better by going through the fire.In this episode, you’ll learn:How legal experience can sharpen sales communicationWhat happens when inbound drops and you’re not readyHow to lead teams closing hundreds of SMB deals per monthThings to listen for: (00:00) Introduction(01:36) What legal training taught him about enterprise sales(04:49) Early sales leadership mistakes at a Series A startup(08:31) How he structured a repeatable outbound pipeline(13:46) Balancing selling and hiring in early-stage roles(15:51) What changed when inbound suddenly dropped(17:24) High-velocity SMB sales explained through a “closing call”(19:59) Shark Tank-style outbound and why it wasn’t scalable(26:18) Finding their ICP using win data, not personas(29:40) Why outbound in SMB SaaS looks very different(34:28) Reps chasing whales vs. reps targeting coral reefs(40:34) Using AI for seller ops instead of seller strategy

Most outbound messaging gets ignored, Reps miss their quota, and the pipeline suffers. Why is this happening?Meredith Chandler, Head of Sales at Aligned, joins Todd Busler to analyze and discuss what it takes to build outbound that actually performs. With experience at Samsara, Spiff, and pclub.io, she shares how her team uses PLG signals to drive pipeline, why reps should build their own 90-day plans, and how coaching shifts from scripts to scorecards.Join us in this episode as she shares all her tips to help sales reps’ outbound messaging reach their goals.In this episode, you’ll learn:How to coach reps to build and own their own 90-day plansWhat makes outbound messaging stand out in crowded inboxesHow to use PLG signals and swarm tactics to generate a pipelineThings to listen for: (00:00) Introduction(01:49) Why selling sales tech is different(03:20) Building outbound from scratch at multiple startups(06:14) How she hit 76% open and 16% booking rates(07:23) Using swarm tactics and memes to drive engagement(09:02) Turning PLG signals into coordinated outbound(10:57) Prioritizing leads with intent scoring(12:07) Aligning BDRs, marketing, and RevOps for plays that convert(15:36) How she creates a high-performance culture(17:11) Coaching reps to think beyond the CRM(18:41) Onboarding reps to 150% quota in their first quarter(20:02) The biggest mistake in most onboarding plans(24:58) Why reps must own their 90-day plan(26:38) Peer coaching and personalized growth paths(28:04) How business acumen drives performance(29:30) Why she coaches outside her day job(31:47) Misconceptions about digital sales rooms(33:43) Selling in a new category without getting outsold

Outdated prospecting playbooks are holding back pipeline growth.Bridget Conneely, Director of NA Business Development at Recorded Future, joins Todd Busler to walk through how her team transitioned from a broad commercial focus to a fully named account strategy. With experience hiring 400+ BDRs and building global programs at Riverbed and Mimecast, Bridget shares how she coaches young talent into high performers. She discusses redefining success metrics, leveraging LinkedIn as a primary channel, and partnering with marketing for an ABM-first model. You’ll also learn about the shift from static product training to story-driven role plays, using small pilots for experimentation, and the importance of personal motivation, AE alignment, and clear scorecards to keep her team focused through change.In this episode, you’ll learn:How Recorded Future moved to a 100 percent named account strategyWhy LinkedIn now drives the majority of the outbound pipelineWhat behaviors predict success in junior reps early onThings to listen for: (00:00) Introduction(01:55) Selling a mission that matters(03:29) Shifting from broad outbound to ABM(05:07) Mapping ICPs using sales and voice data(06:55) Leading BDR change without losing momentum(08:59) How LinkedIn became 80% of the pipeline(12:23) Coaching young reps into confident sellers(16:56) Using story-driven enablement to win deals(20:30) Tying promotion paths to skill-building(22:26) Experimenting with channel-led SWAT teams(25:34) Building high-trust BDR and marketing partnerships(28:54) Traits Bridget looks for in every BDR hire

ChurnZero turned an inbound-heavy team into an outbound machine.Sarah Kiley, Chief Sales Officer at ChurnZero, joins Todd Busler to share how she transformed a historically inbound-heavy sales team into a consistent outbound pipeline engine. With years of experience in government, nonprofit, and EdTech sales, Sarah brings a unique perspective on operational excellence, team culture, and process-driven growth. Sarah shares how she restructured outbound from the ground up, using a process-first approach. She also explains why every rep at ChurnZero now builds their own "sales math" and how personal goals keep their team motivated. In this episode, you’ll learn:How to transition from inbound to outbound without breaking what worksThe role of sales math and personal goals in performanceWhy outbound fails without clarity in process and ownershipThings to listen for: (00:00) Introduction(01:37) Applying for a role that Sarah had to have(03:36) Unlocking customer insights without a CSM team(05:30) The pivot from inbound to outbound(08:09) Culture and clarity during transformation(10:10) Building process without killing culture(12:56) A broken prospecting loop and how to fix it(14:03) Sales math, quotas, and personal goals(17:53) Learning from SDR wins and feedback(23:36) Segmenting reps by market for scale(27:44) How CS teams drive real pipeline(32:51) Missteps slowing down B2B sales orgsBonus for podcast listeners:Champify turns your company’s existing relationships into net-new pipeline—former customers at new jobs, closed-lost deals ready to re-engage, and warm intros that get missed.We’re helping teams like S&P Global generate 20% of their pipeline this way. No complex setup. Just results.Email [email protected] and mention this podcast. We'll run a data test + closed-lost audit to show what you’re sitting on.

Discipline and ownership are the fuel that drives winning sales teams.Toby Carrington, Chief Business Officer at Seismic, joins Todd Busler to share how leading operations, marketing, and SDRs under one roof has shaped his view of modern pipeline generation. With experience scaling global teams and advising early-stage startups, Toby brings a system-level lens to go-to-market execution. He talks about focusing on the structures, feedback loops, and alignment needed to make success repeatable and resilient, regardless of market shifts or company stage.He explains why the best sales orgs prioritize discipline, cadence, and cross-functional alignment, and how personal pipeline ownership has become a leading indicator of rep success. Drawing from Seismic’s enterprise growth journey, he breaks down how platform selling changes rep behavior, coaching, and capacity planning.In this episode, you’ll learn:How Seismic operationalizes rep-led pipeline creationWhy alignment starts with consistent meeting rhythmsWhat behaviors top reps show before the deal closesThings to listen for: (00:00) Introduction(02:51) Unifying ops, marketing, and SDRs for growth(06:42) Feedback loops between product and GTM(08:34) Enablement's rise to the C-suite(13:31) Why rep-led pipeline wins more often(15:01) Cadence and accountability that drive results(21:55) The hidden cost of bad-fit deals(22:19) Selling to all rooms of the house(31:08) PG Tuesdays and focused pipeline bursts(35:44) Cutting AI sprawl with in-flow tools(39:33) Using 1mind to increase inbound conversion

When you’ve been coached by the best, you carry that torch forward.David Boyle, founding partner at RevCentric Partners, shares how a passion for enablement and a history of working alongside sales legends led him to build a consulting firm focused on revenue performance. He reflects on the foundational lessons from PTC and BMC, and why those experiences shaped his approach to pipeline creation and talent development.In this episode, David breaks down the three failure points most CROs face and how to fix them with process, messaging, and consistent live coaching. He explains why sales messaging must be persona-specific, what real adoption looks like, and how great leaders hire and retain top talent by teaching the craft.In this episode, you’ll learn:How to measure pipeline strength with stage two metricsWhat real enablement looks like in practiceWhy coachability matters more than experience in hiringThings to listen for: (00:00) Introduction (02:04) Why sales legends stay in the trenches(04:56) Core habits learned at PTC and BMC(06:49) Three major breakdowns CROs face in pipeline(08:01) How to increase qualified meetings without hiring(09:22) Why most sales messaging never actually works(13:35) Why sales trainings fail without live coaching(17:29) What sellers really want from enablement teams(18:34) How great leaders turn playbooks into performance(22:11) The three must-have traits for every great seller(24:09) Non-negotiable traits every sales hire must have(28:11) Boyle’s response to skeptics of classic sales frameworks

Brian Hamor, CEO of BuyerExperience, shares how a missing answer in a board meeting sparked the idea for his company. He recounts his transition from pro basketball to startup operator and how he uncovered a major gap in how teams handle closed-lost opportunities.In this episode, Brian outlines why win-loss insights alone aren't enough and how revenue teams can turn lost deals into a repeatable growth motion. He explains the rebound funnel, what most teams get wrong after deals fall through, and how AI can be used to re-engage buyers with precision.In this episode, you’ll learn:How to operationalize a closed-lost motionWhat great rebound messaging actually looks likeWhy sales reps must become product expertsThings to listen for: (00:00) Introduction (01:44) From pro basketball to building GTM systems(03:04) The startup moment that sparked BuyerExperience(06:13) Who should lead win-loss: product marketing or sales?(08:33) Why insights aren’t enough without revenue impact(10:15) How top teams build systems to win back deals(12:06) Surprising feedback trends from closed-lost interviews(14:58) Modeling revenue upside from re-engagement programs(19:09) Turning buyer feedback into high-converting follow-up(26:14) Building value cases from AE input before outreach(28:06) When deeper outbound research is worth the effort(30:45) What’s next for BuyerExperience’s product roadmap

Rick Kickert, co-founder and CEO of revlogic, joins Todd Busler to share how his time managing million-dollar budgets shaped a radically different approach to sales. Now advising some of the fastest-growing SaaS companies, Rick brings a buyer-first lens to pipeline generation, sales enablement, and revenue process design.In the episode, Rick shares why chasing massive pipeline numbers often leads teams in the wrong direction, and what top reps do differently to cut through a noisy market. He reflects on a hard-earned lesson from a lost deal that changed how he thinks about differentiation, not as something you sell, but as something you show up with.In this episode, you’ll learn:Why forecasting problems often start with win ratesHow to make every sales stage buyer-facingWhat reps should stop waiting on marketing to doThings to listen for: (00:00) Introduction(02:50) Why most enablement teams get ignored(03:46) Metrics that actually move revenue forward(06:54) What buyers really want from reps(10:31) How and Why AppDynamics hired a buyer to sell(13:59) Impostor syndrome and finding your value(18:16) Mapping sales stages to buyer jobs(24:29) Standing out in crowded markets(30:34) Easy ways to differentiate as a rep(33:08) The painful lesson Rick never forgot

Kyle Asay, VP of Global Growth Sales at LaunchDarkly, shares how he revamped the company’s outbound motion during his first few quarters. He outlines the territory planning shifts, structural changes, and leadership plays that helped drive a 142% increase in pipeline and cut the time to first sale nearly in half.In this episode, Kyle describes how account segmentation set the foundation, what it took to get long-time reps to buy in, and why simple frameworks have helped his team outperform expectations. He also reflects on managing pressure, avoiding whiplash changes, and what it takes to build trust as a new leader.In this episode, you’ll learn:How to transition from inbound to outbound at scaleThe core three metrics Kyle uses to manage performanceWhy territory planning is the key to faster ramp timesThings to listen for: (00:00) Introduction(03:20) Increasing pipeline 142% with outbound segmentation(05:00) Territory planning mistakes and how to fix them(07:50) Getting rep buy-in without causing cultural whiplash(13:12) Leadership lessons from tough feedback and early missteps(16:44) The three outcome metrics Kyle never stops measuring(20:21) Reducing time to first sale through better account focus(23:23) Tracking rep activity without micromanaging(26:52) Turning a feature-led product into a platform story(34:58) Advice on choosing the right sales org and opportunity(36:33) Mastering internal locus of control in your sales career(42:06) Staying grounded as a sales leader in high-pressure roles

More pipeline doesn’t always mean more revenue.Austin Hitchcock, Senior Director of Account Development at Highspot, joins Todd Busler to reveal how he transformed a global ADR organization from product-market fit to a revenue-driving outbound engine. Austin shares the hard truth: more pipeline doesn’t always mean better pipeline. He discusses why conversion rates dropped as the team scaled, the impact of adjusting comp plans to reward qualified opportunities over meetings, and how aligning AE-SDR teams boosted performance on both sides.In this episode, you’ll learn:Why SDR comp plans might be hurting your win ratesHow to fix AE relationships without adding more headcountWhat a modern outbound motion actually looks like in 2025Things to listen for: (00:00) Introduction(01:48) Staying motivated through every company stage(03:51) Scaling SDRs fast and what broke(06:27) Why fewer reps improved outbound results(11:23) Pipeline quality doubled after redefining success metrics(14:48) What top ADRs do after booking meetings(17:10) Why pipeline obsession leads to bad decisions(22:14) How to spot and fix funnel conversion gaps(31:56) How internships fuel long-term sales talent(39:31) Career advice for SDR leaders feeling stuck

Isaiah Crossman, former CRO at Tropic, shares his unique journey from account executive to sales leader, discussing how he led his team through explosive growth. He reflects on the importance of finding the right product-market fit and how his approach to outbound sales evolved from his time at Wunderkind to Tropic.In this episode, Isaiah explains the key role outbound played in his success, the importance of refining sales messaging, and how consistent training and feedback shaped his team’s results. He also dives into the realities of balancing high-volume prospecting with personalized outreach.In this episode, you’ll learn:How to build a high-performing outbound sales teamThe power of consistent training and feedback loopsWhy outbound still works when done rightThings to listen for: (00:00) Introduction (03:06) Isaiah’s background and journey to Tropic(06:12) Joining Tropic as the first sales rep(07:34) The importance of outbound in building the pipeline(14:54) Why outbound is still effective in today’s sales environment(18:38) What differentiates top performers from the rest(25:56) Why generic outbound messaging fails and how to fix it(27:37) Swapping jargon for clarity in sales messaging(29:37) Rethinking disqualification: when pushing leads unlocks hidden value(32:38) A simple two-question framework for effective discovery(40:23) Planting differentiators early to beat your top competitor(43:48) Outpacing larger rivals through service and sales execution

Ryan Heinig, Chief Revenue Officer at 2X, shares his journey from leading top B2B SaaS companies like Qlik and AppDynamics to shaping outbound strategies at a growing tech-enabled services firm. He reveals how he successfully scaled outbound efforts by focusing on repeatable systems, strong leadership, and a balance of empathy and accountability.In this episode, Ryan discusses how shifting from SaaS to services changed his approach to sales, why sales reps must master discovery and qualification, and how to create a culture of high expectations while fostering autonomy.In this episode, you’ll learn:The secret to building a sustainable outbound systemHow to coach your team through real-time sales momentsWhy being empathetic but firm is crucial for sales leadershipThings to listen for: (00:00) Introduction(02:14) Evaluating the opportunity at 2X(04:46) Selling tech-enabled services vs SaaS(06:39) Hiring for curiosity and coachability(08:38) Balancing high expectations with empathy(14:03) Scaling outbound from AE to CRO(17:19) Maintaining PG culture across sales segments(19:25) Leading indicators for outbound success(23:29) Using AI to enhance research and outreach(28:27) Overcoming consistency challenges in outbound(35:31) Defining sales stages that align with buyer’s journey(40:04) Playing the long game in sales

Understanding your buyer changes everything.In this episode, Todd Busler sits down with Em Daigle, Founder & Chief Automation Officer at OTTO-MATES, to talk about what it really takes to sell to accounting and finance professionals.Em shares how her background in public accounting shaped her approach to go-to-market strategy, and why trusted relationships are the key to closing deals in this space. She unpacks what most sales teams get wrong about this audience, how to build long-term credibility, and the value of staying close to your customer.You’ll also hear how product knowledge, curiosity, and patience can transform how teams connect with technical buyers.In this episode, you’ll learn:Why understanding the buyer matters more than urgencyHow to build trust in long, complex sales cyclesWhy education and community are critical for growthThings to listen for: (00:00) Introduction(01:32) Selling to accountants starts with trust(04:06) Why automation needs a human lens(07:31) Learning from messaging that flopped(11:06) Aligning product and sales to win(15:01) Creative events that actually work(20:24) How accountants really want to buy(25:08) Curiosity as a sales superpower(30:36) Adjusting sales motion for new tech(34:00) Building trust through peer-led learning

Outbound sales strategies are evolving faster than ever with AI. The best teams are starting to look inward at their existing data.In this episode, Todd Busler, Co-Founder and CEO of Champify, explores the shifts in outbound sales, particularly the move from traditional email tactics to more personalized approaches. He discusses how cold calling is making a comeback, but with smarter, data-driven strategies behind it. Todd also shares insights on the role of centralizing outbound efforts and why volume-driven plays just aren’t cutting it anymore.It’s a thought-provoking discussion on what’s working in 2025 and beyond, and how companies can adapt their outbound strategy for better results.In this episode, you’ll learn:How the outbound sales landscape is changingWhy leveraging first-party data is key to successThe growing importance of smarter cold calling strategiesThings to listen for: (00:00) Introduction(02:06) The shift from email to cold calls(04:17) Centralized AI-first outbound model explained(05:59) Why automation is losing effectiveness(07:03) Leveraging first-party data for outreach(09:02) Re-engaging closed lost opportunities(11:10) Using closed data for re-engagement(13:52) Why first-party data gives an edge(16:53) The future of personalized outbound outreach

Building a successful sales team goes beyond just numbers.Rob Anderson has built outbound programs at some of the most respected names in SaaS, from scaling Docebo’s SDR engine pre-IPO to shaping enterprise pipeline strategy at Gong. In this episode, he breaks down the systems-level thinking behind it all.At the center of Rob’s approach is his Three E Model: Effort, Efficiency, and Effectiveness. It’s a framework every sales leader can use to pull the right levers, whether you're trying to get more from your reps, improve conversion across the funnel, or adopt tools that map to outcomes.If your outbound motion needs structure, control, and clarity, start here.In this episode, we cover how Rob:Operationalized segmentation before AEs caught upTurned SDRs into embedded deal contributors, not just meeting bookersBuilt systems that scale without bloating headcountThings to listen for: (00:00) Introduction(03:17) Scaling outbound at Docebo(05:05) The importance of phone-first outreach(09:01) Evolving SDR function from small to global(11:14) The power of client stories in sales(15:22) Unlocking insights with technographic data(17:34) Optimizing BDR capacity with AI(20:24) Reworking email strategy for awareness(24:13) Aligning SDR and AE functions(30:12) Shifting role of outbound sales development(33:05) Centralized list-building for SDRs(35:45) Tech tools for modern sales development

How to lead enablement by fixing what’s actually slowing your team down.In this episode, Todd Busler talks with John Ley, Sr. Director of GTM Strategy & Operations at Brex, about what it really means to make enablement a strategic lever from day one.John shares how his time at Square and Brex shaped his thinking, why you need more than playbooks and role plays, and what happens when you build tight feedback loops with sales reps. He gets into how real throughput wins often come from collaborating with teams like finance and risk, not just product marketing or RevOps.You’ll also hear how a practical onboarding framework, strong conviction in your ICP, and a move away from static training decks can unlock meaningful results.In this episode, you’ll learn:How to structure enablement around actual rep painWhy discovery struggles often come back to use casesWhat it takes to build trust as a first enablement hireThings to listen for: (00:00) Introduction(01:44) John Ley’s first priority in enablement at Brex(04:26) Building a reliable foundation for sales data(06:06) Removing friction across ops, finance, and risk(07:33) Rethinking ICP ownership and common traps(10:21) The Brex approach to early outbound plays(13:10) A smarter four-part onboarding for new reps(18:32) Modernizing competitive training with AI tools(22:04) Advice for CROs hiring first enablement lead

Becca Lindquist, Vice President for the Americas at dbt Labs, tells Todd Busler how she helped grow the company from under $1M to over $100M in ARR, and what it takes to scale outbound without gimmicks.In the episode, Becca digs into what separates good sales leaders from great ones: evolving your seat as the company grows, investing early in enablement, and building outbound muscle across the org, not just in the SDR team.In this episode, you’ll learn:Why top reps generate their own pipelineWhat to look for in your first 50 sales hiresWhat makes pipeline council meetings worth doingThings to listen for: (00:00) Introduction(01:13) How Becca stayed in seat to $100M+ ARR(03:01) Adapting your role as the company scales(06:15) Building outbound systems from day one(07:42) Keeping the PG culture as you grow(09:40) Outbound challenges with open source leads(11:34) Teaching reps to spot real business pain(13:24) Scaling enablement without losing impact(19:29) How dbt runs effective pipeline councils(21:52) Making partner selling actually pay off

How to rethink outbound by focusing on quality, efficiency, and what actually moves the needle.In this episode, Todd Busler sits down with Andrew Berger, VP of Revenue at Capchase, to talk through how outbound has changed since the early days of cold calling with a phone book.Andrew reflects on lessons from building Square’s outbound engine, how internal tools and third-party data powered real personalization, and why setting ROI thresholds shaped every decision. He shares the difference between selling to buyers new to financing and those already in the market, and how that distinction drives team structure and messaging.It’s an inside look at how being in the trenches, testing constantly, and rallying around one clear metric are helping the team scale.In this episode, you’ll learn:Why high-volume outbound no longer guarantees resultsHow to use team structure to prioritize pipelineWhat it takes to build trust with executive teams through sellingThings to listen for: (00:00) Introduction(02:28) Breaking into tech through a Craigslist post(04:14) Learning ROI through early sales experiments(06:51) Personalization tactics that actually drove strong results(09:10) Smart tools that streamlined outbound prospecting work(12:45) Leading with investor-style accountability and returns(15:40) Learning to manage with clear expectations(19:37) Splitting playbooks by buyer type and readiness(22:51) Messaging shifts based on market familiarity(30:22) Rallying the team around one weekly metric

Creating a winning outbound sales culture starts with the right ingredients.In this episode, Todd Busler, Co-Founder and CEO of Champify, breaks down the six key ingredients for creating a successful outbound sales motion. He talks about the importance of commitment, setting clear expectations, and maintaining a rigorous process.Todd also highlights how focusing on talent, performance management, and continuous testing can accelerate growth.It’s a practical look at the essential elements that drive a thriving outbound sales culture.In this episode, you’ll learn:The six ingredients for establishing a thriving outbound sales cultureWhy a top-down commitment is crucial to successBest practices for skill development and talent managementThings to listen for: (00:00) Introduction(02:26) Six essential ingredients for outbound success(04:34) Establishing a consistent operating cadence for strategy(05:29) Role of revenue operations and support for success(09:23) Motivating the team with rewards and recognition(13:02) Acquiring top talent and effective hiring strategies(15:02) Consistent performance management practices(17:21) No single solution; strong culture is key(18:23) Focus on cold calling and AI preparation

What actually makes an outbound sales engine run at the enterprise level?In this episode, Todd Busler sits down with Zack Sikora, GVP of Sales at Benchling, to talk through what consistent pipeline generation actually looks like at the enterprise level.Zack shares how his time at AppDynamics shaped his thinking around qualification, why AEs must own outbound, and how activity signals can tell you everything you need to know about performance. He also opens up about building a culture where creativity is celebrated, enablement is a priority, and leaders know when to step aside and let reps lead.It’s a front-row look at how structure, storytelling, and small wins can power serious sales results.In this episode, you’ll learn:How to create a PG culture centered on AE prospecting that lastsWhat to track across the sales cycleWhy enablement is your secret advantageThings to listen for: (00:00) Introduction(01:39) Zack’s path through elite sales orgs(02:50) From hardware sales to value selling(05:37) Using activity signals to guide coaching(08:02) Pairing EQ with a process-driven mindset(11:18) Sharing small wins to fuel PG culture(15:03) Leading with outcomes over features(20:19) Why AEs must own their outbound motion(29:37) Enabling sellers with tailored bootcamps(34:33) What outbound could look like with AI

Building a sales system that drives repeatable growth takes structure.In this episode, Todd Busler talks with Mark Niemiec, CRO at Salesloft, about the power of sales scaffolding. Mark shares how zeroing in on Salesloft’s mission—helping sellers win—sharpened their focus and fueled real results. He dives into how blending big-company infrastructure with small-company hustle created a high-performance culture. You’ll also hear him unpack how a bold new narrative and better tools empowered reps to land bigger, more strategic deals.It’s a behind-the-scenes look at the strategies driving Salesloft’s sales team to scale and stay aligned.In this episode, you’ll learn:How to build a sales scaffolding system for predictable successWhy creating a singular focus leads to massive sales impactWhen to make the jump from sales planning to sales executionThings to listen for: (00:00) Introduction(05:46) Streamlined teams improve efficiency and morale(07:24) Optimizing sales: people & pipeline(12:13) Revamping sales strategy: expanding beyond cadences(16:00) Elevating customer engagement techniques(18:42) Compensation strategy focuses on customer succes(20:56) Revitalizing sales team engagement strategy(23:24) Data-driven marketing collaboration strategies(27:44) Blending artistry with engineering rigor(31:29) Efficient storytelling boosts business strategy(35:11) Blending creativity and data in sales approach (36:40) Culture's role in business success.

How to build a SaaS company from scratch with a sales-focused mentality from day 1.In this episode, Todd Bustler talks with Alex Olley, Co-Founder and CRO of Reachdesk, about what it really means to build a go-to-market motion from scratch.Alex gets into the bold outbound bets that paid off, why attribution debates are a distraction, and how one smart RevOps hire changed the game. He also breaks down how tightening their ICP—and giving frontline teams a seat at the strategy table—helped Reachdesk hit its stride.It’s a behind-the-scenes look at how a little chaos, ownership, and constant testing fueled their early sales motion.In this episode, you’ll learn:How to scale pipeline without relying on inboundWhat a “caveman strategy” looks like in modern salesWhen it’s time to rethink your hiring and team structureThings to listen for: (00:00) Introduction(01:31) Founding Reachdesk and choosing the CRO path(05:15) The caveman strategy behind early sales motion(10:56) One-to-one personalization that drove real results(12:43) How a RevOps hire unlocked next-level growth(16:06) Narrowing the ICP using clear buyer signals(24:03) Giving the front line a voice in GTM decisions(27:06) Why “Allbound” beats attribution arguments(33:38) Testing verticals with a focused outbound squad(35:57) What Alex would do differently if starting today

How do the best companies build outbound machines that actually work?If you think outbound is dead, you’re either lying or you’re bad at it.I’m Todd Busler, former VP of Sales turned co-founder of Champify, and I’ve spent my career building repeatable systems that drive real pipeline.On this show, I’m talking to sales leaders who have cracked the outbound code and created an outbound culture within their companies.If you’re tired of guessing and ready to build an outbound motion that actually delivers, hit subscribe. Let’s crack this thing wide open.