PODCAST · business
How I Deal
by Taylor Dahlem
Get the good, the bad, and the ugly of past deals from real B2B Account Executives in the trenches daily: Taylor, an AE turned content guy, and Junior, a full-cycle sales superstar. From initial LinkedIn research to the final PDF signature, they chat with fellow reps and dive into every step of a single deal. Leave with focused tips to implement in your sales game today and enjoy "closed-won" war stories.
Episodes
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Tanner Lacey @ Sales Assembly (#49)
Tanner re-lives the first large enterprise deal he landed for his startup. When selling in a company's early stages, it truly takes a village to get an enterprise deal across the line. You have no SOPs, legal red-lining & security protocols. Just a strong team, 100% focus, & a vision. That's how...
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Jeanna Humble @ Gamify (#48)
Jeanna walks us through a true sales albatross: closing the biggest deal in his company's history in their fastest sales cycle ever. If closing a massive deal in 2 weeks sounds insane, that's because it is. But that is exactly what happened to Jeanna & changed the course of his selling career....
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Morgan Buchanan @ Spekit (#47)
Morgan heads back to her non-profit roots in this one. Selling into an Austrialian-based non-profit & working through several firsts. Her first international deal & totally outside her typical ICP. But in any down market, you have to be flexible as a seller & take chances on any lead. Morgan did...
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Chris Horton @ Workstream (#46)
Chris is the adventurous tech sales guy. In between climbing mountains, he's closing enterprise deals. He re-lives a wild deal involving one of the largest restaurant groups in the United States. He took the risk of flying out to a conference to 'run' into the prospect CEO 7 open the dialogue....
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Laura Erdem @ Dreamdata (#45)
Laura has been transitioning as a seller from enterprise sales to growing a startup, moving from founder-led sales to rep-led sales. While so much has been in flux, one thing remains true: people buy from people they trust. In order to build that trust, Laura has become an expert in social…
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Krysten Conner @ UserGems (#44)
Krysten re-lives a deal that showcased every major aspect of why enterprise deals close: executive alignment, multi-threaded & single-threaded, involving every buyer type from top to bottom. She took this deal over mid-flight from a colleague & had to grab the baton smoothly before things fell...
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Cassandra Freeman @ Velocity Access (#43)
Cassandra talks through the first closed-won deal for her & her company! Sales reps typically avoid being the first to venture down the path of selling a new persona, but not Cassandra. She sourced this opportunity from a past closed-lost deal & strong partner relationships. Dive into the…
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Justin Jay Johnson @ FitGrid (#42)
Justin reminisces on a mega-deal missed opportunity from his Salesforce.com days. We're talking eight figures. From working with the prospect daily for a year, building a case for a $15MM digital transformation deal, & working with Marc Benioff. This deal had everything except a final signature....
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Max Tierney @ MongoDB (#41)
Max takes us through a deal containing true champion-building efforts. Both internal & external. Internally, he built a deep connection with his Solutions Engineer. They worked this deal together better than Jordan & Pippen. Externally, Max fostered a powerful relationship with the prospect's Dev...
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Christian Erba @ Contractbook (#40)
Christian walks us through his first closed-won as an AE! In the midst of a company-wide persona shift, Christian worked through deep research & LinkedIn Sales Nav like a true pro. Surfacing this international deal from nothing & closing it through dedicated personalization. Hear how he did it!...
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Morgan Shelly @ Tray.io (#39)
Morgan re-lives her first closed-won deal ever! Transitioning from full-time teacher to full-time seller wasn't easy, but leveraging transferable skills & a killer PLG motion ended up being the difference. Providing proof of value & taking a calculated risk to create palpable urgency led to the...
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Andrés Angulo @ Apollo.io (#38)
Andrés typically works inbound leads, so this particular deal stood out as a highly strategic outbound effort on his part. He leveraged multi-threaded voice memos via LinkedIn, ran a truly thorough discovery process, & delivered a personalized demo (outside of the standard one his company…
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Jack Ryan @ SaaStr (#37)
Jack talks through a deal he closed that equated to SaaStr's largest outbound sponsorship deal to date. Leveraging a teammates podcast, Crunchbase, & in-person meetings at SaaStr itself, Jack worked this deal with incredible precision. Even with major bumps in the road. Namely, red tape, waiting…
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Axel Zaccardo @ Contractbook (#36)
Axel re-lives a prospect look-alike deal he masterfully executed. Coming off the momentum of a recently closed inbound deal, Axel didn't sit back. Leveraging LinkedIn Sales Navigator, he found a prospect who might be dealing with similar issues. Using the social proof of the inbound competitor &...
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Charlotte Lloyd @ Simply Sales & Marketing (#35)
Charlotte takes us down memory lane to a deal where the juice wasn't worth the squeeze. Selling to city locations & governments is a mixed bag. While cool to with mayors & governors, the red tape can sometimes be a nightmare. Hear how she navigated the process & eventually got it inked. Featuring...
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Rocco Savage @ regie.ai (#34)
Rocco re-lives a deal that began in an excellent economy & closed in a down economy. On top of that, he sold a little-known product category at the time. So education and quantifiable value were key. Hear how Rocco brought this buyer back from ghosting with a pen in hand to sign. Featuring DiSC...
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Neal Goyal @ Tapcart (#33)
Neal takes us through the deal that got away. Marking our 2nd closed-lost episode. This one is just as jam-packed with tough lessons learned. Working with some of the top brands in the world, sometimes you can assume you know a prospect's problem before asking. But that can be a costly mistake....
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Mor Assouline @ FDTC (#32)
Mor had to close an enterprise sale within a month or his business would close. He re-lives the buzzer-beater deal that kept his dream alive with us. Talk about pressure. Want to improve your buyer persona research? This is the episode for you. Featuring toy commercial strategy, demo win rates, &...
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Scott Knudson @ Clozd (#31)
Scott chats through the deal that got him to his first Presidents Club trip. As a long-time individual contributor, now Sales Enablement head, a lot of his sales training & enablement approach is based on the lessons he learned in this particular deal. Featuring sales trap setting, 20/20…
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How I Deal Highlight Show! (#30)
How I Deal has hit the big 3-0! To celebrate, we've compiled a few great clips from the previous 29 episodes. From initial account research to the final signature, hear some of the top takeaways from full-cycle sellers each step of the way. Featuring: Ricky Pearl - Building GTM prospect lists Cam...
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Zeke Lucas @ RentDynamics (#29)
Zeke is not your typical sales rep. He takes us through the first deal he won after only 30 days into his new role. How did he land this one so quickly? A combination of insane levels of research & the ability to be thoughtfully aggressive. But this is a 2-part land & expand deal & things got…
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Alex Lee @ Via (#28)
Alex has been in sales for years but has never sold into the non-profit world, he walks us through his first experience. While never afraid to call a C-Suite, he isn't a fan of the RFP process. But this deal gave him a healthy dose of both. After a 60-slide demo (webinar style) & negotiations…
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Will Aitken @ Sales Feed (#27)
Will recants winning a deal that he preferred to walk away from instead. It was the classic enterprise deal eyes with an SMB stomach. When a Fortune 100 company comes inbound, it's hard not to bite. But make sure you truly understand how decisions are made & the procurement process to win the...
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Stephanie Sanders @ Contractbook (#26)
Stephanie re-lives her very first closed-won deal at Contractbook. A casual, but timely, practice pitch to a friend led to a warm intro with the decision maker & the sales cycle accelerated from there. Steph was along for the ride & brought in her team to help get the final signature. Featuring...
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Logan Amstey @ Sequel (#25)
In true spooky season fashion, Logan takes us through a sales nightmare: a closed-lost deal! After a standing Friday discovery meeting for over a year, Logan walked away from the deal due to the sheer ROI resource-suck. He re-lives what could've gone differently & how he's applied those lessons…
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Nate Nasralla @ Fluint.io (#24)
Nate lays out a true guidebook to helping a buyer step into life after the solution. As we know, sales is storytelling, but the art of visualization is a base requirement. Nate is one of the best & details of how he navigated a demo to a proof-of-concept experience which led to a huge closed won...
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Patrick Kennedy @ Funnel (#23)
Patrick takes us through his favorite deal since moving from sales leadership to individual contribution. Selling into the Fortune 100 equivalent of the multi-family space, he had his work cut out. Over 8 months, he leveraged conference networking, added value in dark periods, & delivered an...
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Anthony Natoli @ Lattice (#22)
Anthony re-lives a rollercoaster ride of an enterprise deal. Leveraging a custom account plan while dividing & conquering with his mighty SDR, Anthony created an amount of value that no competitor price-drop could touch (oh how they tried). Featuring account plans, scary ghosting, & a talented...
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Blaise Bevilacqua @ UserGems (#21)
Blaise shows us the way to practice what you preach & using your own product to sell. The proverbial 'eating your own dog food'...if you will. After discovering a current customer moved to a new role at another company with UserGems, Blaise jumped right in with a highly targeted message & was...
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Josh Patiño @ Funnel (#20)
Josh walks us through his first closed deal at Funnel (and first deal as a sales pro)! In the midst of learning two industries at once (property management & sales in general), Josh discovered the link that connects them all: telling a story. Putting his new skills to the test, hear how he…
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CJ Friedrichs @ High5 (#19)
CJ re-lives his the first deal he closed in the first 90 days at High5. Relying on his team to be the SME (subject matter experts), CJ saw an opportunity to take on the quarterback role & has changed his approach to deal-making ever since. Featuring an 18 min cold call, an agenda-setting...
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Cam England @ Clozd (#18)
Cam takes us on a 20-month sales redemption story. After crashing & burning one of his first opportunities at Clozd, he learned from past mistakes. Taking more at-bats & returning to the deal to ultimately close it in the end. Featuring wild west prospecting, Gap Selling redemption, & a heavy…
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Lesley Klose @ FitGrid (#17)
Lesley re-lives her first multi-location deal at FitGrid in this one! Detailing her evolution from yoga instructor & FitGrid power user to joining their sales team to grow a product she personally believed in. Her unorthodox journey has served her well in building trust & lasting relationships…
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Bradley Paster @ Guardsquare (#16)
Bradley talks through a random inbound lead that turned into the single largest transaction in their company's history. Featuring Bradley reverting back to a closing role as a Sales VP, a death in the family mid-deal & the rest of the team rallying together to bring it across the finish line as a...
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Spencer Wuthrich @ Clozd (#15)
Spencer walks us through the most mentally challenging deal of his career. This mid-market deal came from an old opportunity that went with a competitor a year prior & decided they fell victim to over-promise, under-deliver tactics. Featuring webinar prospecting perfection, lock step his sales...
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Ricky Pearl @ Pointer (#14)
Ricky guided a deal with one of the biggest companies in the world from a cold, generic email to a $100 million contract in 3 short years (haha). Navigating endless buying committees, constant turnover, & strict covid protocols; Ricky managed to land the sale without ever meeting the final…
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Amy Hrehovcik @ Revenue Real Hotline (#13)
Amy took a huge risk setting her sights on a massive deal in the legal sector that had never been attempted by anyone at the company before. The multi-quarter deal consisted of 10+ meetings & buyer types, several trips between NYC & LA, all while dealing with internal pushback around the expense…
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Nick Smith @ WorkSpan (#12)
Nick, who's sold services his whole career, chats through his first-ever product closed deal. While the transition seems small, there's a ton of nuance that goes into each version of the sales cycle. Especially considering the deal metrics & overall size of the opportunity (1,000+ employees).…
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Amelia Taylor @ Carabiner Group (#11)
Amelia takes us through the most unorthodox deal she has ever worked. A redemption story that started off with getting her hand slapped by her prospect for "pitch slapping" in his Slack community all the way to closing the deal through her CEO who happened to be sitting next to her prospect's CEO...
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Taylor Shaffer @ QuotaPath (#10)
Taylor takes us through a near-perfect SMB deal that came inbound. From webinar to closed-won, Taylor discusses how she identified the opportunity, leveraged valuable content to open a window, & built a strong solution-focused relationship over a few weeks. She overcame the barriers of working…
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Nolan Hansen @ Workfront (#09)
Nolan discusses a $500k enterprise deal that started with a few teams & eventually grew to multiple hundreds of users. After literally writing the Request For Proposal for them, running discovery meetings with 15 decision-makers, & hosting a 3-day on-site demo; he still almost lost this massive...
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Kaylee Chappelow @ Greenhouse.io (#08)
Kaylee re-lives her first-ever enterprise deal! As an early sales hire at a growing startup, she had to take the reigns from the founder-led sales motion & trailblaze the next phase of the company. Kaylee had to take an inversed multi-threaded approach to close this one & even had to overcome...
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PJ Ricketson @ Adobe (#07)
PJ explains how he landed his first mammoth-level deal after running a targeted, education-led nurture campaign. To get it across the finish line, he had to overcome the fact that his internal champion previously worked at their biggest competitor & navigate the complex legal structures of a…
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Gerry Hill @ ConnectAndSell (#06)
Gerry explains how he landed a massive logo during a recession with a hyper-targeted cold call. He also never demoed the platform until after the deal closed. Think selling in a down market is impossible? Gerry lays the roadmap to do just that in this episode. Gerry's 3 Sales Takeaways (No...
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Gavin Tice @ ConnectAndSell (#05)
Gavin explains how he landed a $200k deal in just one cold call & two meetings. If you thought cold calling was dead...Gavin will bring it back to life before your very ears. Gavin's 3 Sales Takeaways (No Spoilers!): Be gusty 5 minutes at a time. Ask tough questions that make even you...
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Greg Cammarata @ demandDrive (#04)
Greg Cammarata explains how he snatched a deal from the jaws of an acquisition. Truly GOAT-level deal-making packed into this one. Greg's 3 Sales Takeaways (No Spoilers!): Work smart once the opportunity is in the pipeline. Do your homework on every aspect of the buyers & the company. Honesty &...
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Melanie LaCombe @ AirDeck (#03)
Melanie LaCombe takes Taylor & Junior through a rollercoaster enterprise deal. With multiple stakeholders, a fast timeline, & a huge roadblock; re-live how this deal went from "old gold" to her largest "closed-won" sale in just 4 months. Melanie's 3 Sales Tips (Summary): Creativity can go a long...
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Maggie Blume @ Mailshake (#02)
Maggie Blume takes Taylor & Junior through an epic inbound lead journey. Stretching over a year, but led to a solid closed-won deal. Utilizing her own platform, Mailshake, Maggie built personalized nurture sequences to keep the buyers engaged until the timing was perfect. Have a deal in your...
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Junior Lartey @ Pickle (#01)
Junior Lartey dives into a deal he won after showing up after the buyer was in VERY late stages with his biggest competitor. From initial LinkedIn research to the signed PDF, he talks through how he won them over while providing tips you can try today!
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ABOUT THIS SHOW
Get the good, the bad, and the ugly of past deals from real B2B Account Executives in the trenches daily: Taylor, an AE turned content guy, and Junior, a full-cycle sales superstar. From initial LinkedIn research to the final PDF signature, they chat with fellow reps and dive into every step of a single deal. Leave with focused tips to implement in your sales game today and enjoy "closed-won" war stories.
HOSTED BY
Taylor Dahlem
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Frequently Asked Questions
How many episodes does How I Deal have?
How I Deal currently has 49 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is How I Deal about?
Get the good, the bad, and the ugly of past deals from real B2B Account Executives in the trenches daily: Taylor, an AE turned content guy, and Junior, a full-cycle sales superstar. From initial LinkedIn research to the final PDF signature, they chat with fellow reps and dive into every step of a...
How often does How I Deal release new episodes?
How I Deal has 49 episodes. Check the episode list to see recent publication dates and frequency.
Where can I listen to How I Deal?
You can listen to How I Deal on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts How I Deal?
How I Deal is created and hosted by Taylor Dahlem.
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