How I Deal: Recent Episodes
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 & enjoy "closed-won" war stories.
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 Tanner brought this one home. Listen to the full story!
Featuring neighbor referrals, SAP, & the Jamaican legal system
Tanner's Sales Tips
- Invest in relationships over everything
- You can never be 'over-threaded' in a deal
- Confidence goes a long way. Especially as a startup
Tanner Lacey: https://www.linkedin.com/in/tanner-lacey/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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. Listen how!
Featuring gamification, Charles Barkley, & multiple languages
Jeanna's Sales Tips
- Relationship building is everything in sales
- Opt to be genuine over a people pleaser
- Be like a goldfish. Lost a deal? Move to the next one
Jeanna Humble: https://www.linkedin.com/in/jeanna-lifungula-humble-a25b00106/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 exactly that. Paid off big time!
Featuring selling in a down market, international intrigue, & a pitbull rescue
Morgan's Sales Tips
- Consider all potential impacts & outcomes blocking a deal
- Dip into past experiences to find new opportunities
- Stay up to date on every past deal. Prioritize look-alikes
Morgan Buchanan: https://www.linkedin.com/in/morganbuchanan1/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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. Leading to a chain of events that allowed him to mark it closed won. Hear how it went down!
Featuring a risky trip, free food for life, & rock climbing
Chris' Sales Tips
- Put yourself in your prospect's shoes. Would you buy?
- One door closes, another opens. You gotta walk through.
- Always be authentic. Don't need to button up to sell.
Chris Horton: https://www.linkedin.com/in/christo-horton/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 selling. She appears everywhere her buyers live online before they even know they're ready to buy. Being there for them with education-led conversations leads them to go to Laura first when they are ready to buy. That's exactly how she closed this deal. Have a listen!
Featuring proof of concept, enterprise to startup sales, & March Madness
Laura's Sales Tips
- Care about your prospects. It's that simple.
- Master open ended-questions.
- Live where your buyers live.
Laura Erdem: https://www.linkedin.com/in/lerdem/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 apart. Hear how she quickly caught up to speed on the details/personalities & brought the deal home.
Featuring single threading, mid-deal takeover, & teachers
Krysten's Sales Tips
- Align your executives & the buyers. Your VP should know their VP.
- Thread all 3 levels: user, manager, & executive
- Team selling is dream selling
Krysten Conner: https://www.linkedin.com/in/krystenconner/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 metaverse with us & hear how it went down!
Featuring the metaverse, partner-led sales, & TikTok dogs
Cassandra's Sales Tips
- Strive to be the expert in any field you sell into.
- Don't focus on other sales reps' careers. Your journey is unique.
- Work like someone else wants your job. Cause they do.
Cassandra Freeman: https://www.linkedin.com/in/cassandrarfreeman/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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. Learn how it all went down.
Featuring digital transformation, the Amazon Death Star, & Auntie Anne's Pretzels
Justin's Sales Tips
- Even in a team sale, the deal falls on the rep to close.
- Find the deal red flags as soon as possible.
- Win or lose, learn everything you can working a huge deal.
Justin Jay Johnson: https://www.linkedin.com/in/justinjayjohnson/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 Ops team & gave them to confidence to sell it to the CEO themselves. Hear how it went down!
Featuring deal progression meetings, TCO, & the Kansas City Chiefs
Max's Sales Tips
- Be creative with outreach & interrupt patterns.
- Bring an opinion to the table. They will correct you. (great!)
- Build a business case with your champion.
Max Tierney: https://www.linkedin.com/in/max-tierney-86762010a/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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!
Featuring lawyers, Series C funding, & goin' full Super Saiyan mode
Christian's Sales Tips
- Create avenues to solve multiple problems.
- Set the tempo with consistent, timely responses.
- Be brutally honest about your product.
Christian Erba: https://www.linkedin.com/in/christian-erba-a949191ba/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 Docusign being completed.
Featuring teaching to sales, proof of value, & Argentina
Morgan's Sales Tips
- Need urgency? Turn off the trial
- Lean into value selling. Speak benefits, not features
- Align business & technical solutions consistently
Morgan Shelly: https://www.linkedin.com/in/morganshelly/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 expects). That approach & risk landed him the signature. Hear how!
Featuring product-led prospecting, voice notes, & contemplative monks
Andrés' Sales Tips
- Leverage job changes. Top-tier buying trigger.
- Be patient. Allows you to be more strategic.
- Avoid superficial discovery. It's all about them, not you.
Andrés Angulo: https://www.linkedin.com/in/andres-angulo-growth/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 on an executive new hire, and budget concerns. Hear how he closed this one.
Featuring Crunchbase, podcast prospecting, & photography
Jack's Sales Tips
- Be relentlessly persistent in everything you do.
- When it comes to quota, consistency > hot/cold streaks.
- Adjust follow-up to market conditions & a human touch.
Jack Ryan: https://www.linkedin.com/in/paralyzed-to-peaks/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 & the hypothesis of similar pain, he was able to get in front of the buyer immediately & close another deal in under 3 weeks. Hear how he did it.
Featuring sales humor, electric vehicles, & speaking Icelandic
Axel's Sales Tips
- Ask for the next step. If there's value, don't wait.
- Always run deals with authenticity. Trust builds faster.
- Nobody cares about features. Personalize to their workflow.
Axel Zaccardo: https://www.linkedin.com/in/axel-zaccardo/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 100% commission, a rough cold email, & Canada
Charlotte's Sales Tips
- Detach yourself from the outcome. Deals ≠ your self-worth.
- Don’t withhold the price. Let the prospect determine their value.
- Disqualify to qualify. Always ask: Is the juice worth the squeeze?
Charlotte Lloyd: https://www.linkedin.com/in/charlottelloydsales/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 profile, Objection vs. Situation, & Tony Robbins
Rocco's Sales Tips
- You're hired to sell. No matter what economy we're in
- Keep 1 ear to the sky. Know what impacts prospects (macro)
- Keep 1 ear to the ground. Be mindful of your prospect's reality (micro)
Rocco Davage: https://www.linkedin.com/in/roccosavage/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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. Hear how.
Featuring riding the hot hand, video prospecting, & A-list celebrities
Neal's Sales Tips
- Spend time re-living missed opportunities. Learn more that way.
- Listen more than you speak. Empathy wins over features often.
- Know where you stand competitively at all times.
Neal Goyal: https://www.linkedin.com/in/nealgoyal/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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, & an '8 Mile' reference
Mor's Sales Tips
- Assume every lead isn't a fit right away. Your discovery calls will thank you.
- Take an obnoxious amount of notes about the most minor details.
- Don't ask for the sale (money). But always ask for the close (next step).
Mor Assouline: https://www.linkedin.com/in/morassouline/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 hindsight, & knucks with the pope
Scott's Sales Tips
- Innoculate objections before they arise. "Here's what you're gonna say..."
- People buy based on experience. Keep that top of mind constantly.
- Setting next steps is a muscle you have to exercise consistently.
Scott Knudson: https://www.linkedin.com/in/scotttheamazing/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 England - LinkedIn Sales Nav 101
Maggie Blume - Don't sleep on inbounds
Nick Smith - Keep emails painfully short
PJ Ricketson - Discovery questions = deal trajectory
Patrick Kennedy - Mobilzers vs. Champions
Nolan Hansen - On-site demo magic
Amelia Taylor - Running deals via Slack
Nate Nasralla - Negotiating with you own team
Help us out!
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 rocky in between. Hear how it all went down.
Featuring land & expand, framework mastery, & street photography.
Zeke's Sales Tips
- Be aggressively thoughtful. Allows you to follow up frequently.
- Build frameworks so you can think less & organize more.
- Upsell potential? Jump on those post-sale meetings to drive value.
Zeke Lucas: https://www.linkedin.com/in/residentjourney/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 with a gaggle of lawyers, Alex closed this thing out.
Featuring a 60-slide webinar, being out-lawyered, & a watch collection.
Alex's Sales Tips
- Never count yourself out in an RFP. You can always find a way to win.
- The more people you involve, the better chance it closes.
- Never underestimate human emotion in sales. Not always hard #'s.
Alex Lee: https://www.linkedin.com/in/alex-lee-nyc/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 business.
Featuring qual-call downfall, enterprise eyes/SMB stomach, & a Scratchpad tattoo.
Will's Sales Tips:
- Don't chase shiny objects. Small deals in large companies aren't always worth it.
- Legal is an ally, not an enemy. They want to close the deal as much as you do.
- Structure meetings well. It'll be the difference between you & a competitor.
Will Aitken: https://www.linkedin.com/in/justwillaitken/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 pain vs. future focus, referral 101, & fear of turbulence.
Steph's Sales Tips:
- Practice your pitch with friends. Never know where it'll lead.
- Demo their process within your product.
- Control what you can. Your process & communication style.
Stephanie Sanders: https://www.linkedin.com/in/stephdsanders/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 to other deals.
Featuring a pros-cons list, 35+ meetings & a love for pottery.
Logan's Sales Tips:
- Buyers are emotionally-driven. Logic can sometimes take a back seat.
- You can always bring more stakeholders to the table. It's worth the effort.
- Know what your time is truly worth & when to walk away from a deal.
Logan Amstey: https://www.linkedin.com/in/loganamstey/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 deal.
Featuring 1 cold email, demo vs. proof-of-concept & Honduras
Nate's Sales Tips:
- Use written material to increase communication speed with executives.
- Help prospects experience life inside your product, don't just demo it.
- Know when to stop selling.
Nate Nasralla: https://www.linkedin.com/in/natenasralla/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 incredible buying experience.
Featuring the ol' land/expand v. top-down debate, mobilizers, & getting lawyered
Patrick's Sales Tips:
- Discovery is an ongoing & fluid process. Ask questions before, during, & after meetings.
- Don't get caught single-threading. Find your mobilizers & champions.
- Embrace the ghost periods. Continue to provide value until their ready.
Patrick Kennedy: https://www.linkedin.com/in/patrickkennedy-pk/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 procurement officer.
Anthony's Sales Tips:
- Get to the friction ASAP. Why would they say 'no'? Only hearing 'yes' = a red flag.
- Hold micro-meetings with the prospect before deal milestones. Ensure you're on track.
- Multi-thread internally as much as you do with your prospect. Loop teammates in.
Anthony Natoli: https://www.linkedin.com/in/anthony-natoli/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 introed to the movers & shakers at the top of the totem pole. Leveraging a powerful champion, customer stories, & a lot of data; the deal closed in just 3 weeks.
Featuring a whole lotta UserGems, raw data, & the 'Tech Stack Governor'.
Blaise's Sales Tips:
- Stay on top of prospect job changes. Automate where you can.
- Get to a personal level. Texting > email in later stages.
- Prospect top down. Faster sales cycles & fewer barriers.
Blaise Bevilacqua: https://www.linkedin.com/in/blaise-bevilacqua/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
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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 uniquely approached each step of the sales process to paint a clear picture and tap into the power of storytelling to close this one.
Featuring the sales gods, creative use of Lucid Chart, & secret shopping apartments.
Josh's Sales Tips:
- Dig deeper by answering a question with a question.
- Never leave a meeting without the next meeting set.
- Set clear objectives before every conversation, but be flexible.
Josh Patiño: https://www.linkedin.com/in/joshpatino/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
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We love connecting with our listeners & always look to improve!
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 masterclass, & the word 'headwinds'.
CJ's 3 Sales Tips:
- Strive for a casual text-level relationship with prospects.
- If urgency is needed, keep messaging prospect-centric & creative.
- Expect the unexpected in sales. Things will go wrong. Roll with it.
CJ Friedrichs: https://www.linkedin.com/in/charlesfriedrichsjr/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
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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 dose of Sales Navigator tips.
Cam's 3 Sales Tips:
- Persistence is everything. Value-add follow-up until the deal closes.
- Quantifying pain in discovery is the foundation of every sale.
- Always be learning personally & professionally.
Cam England: https://www.linkedin.com/in/cam-england/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
Check out the How I Deal podcast content hub: https://www.pickleai.com/how-i-deal-podcast
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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 with her fitness studio clients. Featuring a buyer burned in the past, practicing what you preach (literally), and Bikram yoga.
Lesley's 3 Sales Tips:
- Under promise & over deliver. Tee up your customer teams to crush it.
- Be honest, human, & relatable at all times in the process.
- Sell something you love. The grind is much more fun when you're passionate.
Lesley Klose: https://www.linkedin.com/in/lesley-klose-333633152/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
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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 result. Balancing sales performance & mental health is at the forefront of this conversation. We need to talk about it as revenue professionals more, but this is a start.
Bradley's 3 Sales Tips:
- Build a process each step of the way & stick to it.
- Engage your internal teams early & often. Both your team & the prospects.
- Don't be an ass. Empathy over everything in sales.
Bradley Paster: https://www.linkedin.com/in/bradleypaster/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
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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 engineer & weaponized FOMO (fear of missing out). Hear how this sale played out!
Spencer's 3 Sales Tips:
- Prioritize empathy in all deal stages. Walk in their shoes.
- Avoid needing to sell a prospect more than they want to buy.
- Big deals take time to close. Create multiple paths to quota.
Spencer Wuthrich: https://www.linkedin.com/in/spencerwuthrich/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
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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 decision makers. This is our longest episode to date & for good reason. Learn from one of the most professional salespeople we've had the pleasure of chatting with!
Ricky's 3 Sales Tips (No Spoilers!):
- Multi-thread to the point you've found yourself on their buying committee.
- Take the time to map out every aspect of their decision-making process.
- Motivating factors aren't always growth, often it's purely risk avoidance.
Ricky Pearl: https://www.linkedin.com/in/rickypearl/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
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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 of this deal compared to the likelihood of landing it. Amy, using every bit of her green belt in process management, close this thing out & became a company legend. Hear how it all went down!
Amy's 3 Sales Tips (No Spoilers!):
- It takes a village to help a sales pro. Landing any deal is a true team sport.
- Preparation, preparation, preparation. That's the tweet.
- Take risks & lean into discomfort. Not failing = not learning.
Amy Hrehovcik: https://www.linkedin.com/in/amyhrehovcik/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
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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). Nick did his homework, knew his persona in & out, & overcame a few barriers along the way. Hear his story!
Nick's 3 Sales Takeaways (No Spoilers!):
- Get in front of the timeline. Prepare for & confront barriers before they set you back.
- Deals are fluid. Listen & adapt. Don't ask a question just to check a box.
- Be creative & interrupt patterns in your outreach. Don't just send 100 emails & call it a day.
Nick Smith: https://www.linkedin.com/in/nickreedsmith/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
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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 at a conference. How'd she do it? Give the episode a listen!
Amelia's 3 Sales Takeaways (No Spoilers!):
- Don't give up if you think you've lost a deal. Barriers always come up; but where a door closes, another opens.
- Don't be intimidated by titles. C-Suites are always looking to learn, AE's can provide those lessons too.
- Match relevancy with personalization. There's always buying trigger, find it & add your own flair to the message.
Amelia Taylor: https://www.linkedin.com/in/amelia-taylor1/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
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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 with an international company & a CEO who was weary of buying any new software by truly understanding the root problem while clearly communicating how she could help solve it. How'd she do it? Give the episode a listen!
Taylor's 3 Sales Takeaways (No Spoilers!):
- If your prospect is engaged, don't cut the conversation short. If possible, go over time & answer every question.
- Always have 2-3 value touches to stay top-of-mind between meetings.
- Don't be afraid to discount strategically if it gets the deal done (with approval of course).
Taylor Shaffer: https://www.linkedin.com/in/taylorshaffer16/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
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We love connecting with our listeners & always look to improve!
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 deal due to a brand new executive trying to make their mark. How did he save it? Well...you'll have to listen to the episode.
Nolan's 3 Sales Takeaways (No Spoilers!):
- There's no magic bullet to meeting quota. Just consistency over time & a lot of elbow grease.
- Be more like a consultant, less like a salesperson. Help them uncover solutions, not just problems.
- Rely on your internal ecosystem. No matter the size, every company has resources you can use.
Nolan Hansen: https://www.linkedin.com/in/nolan-hasen/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
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We love connecting with our listeners & always look to improve!
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 executive buyer turnover mid-deal. How did she do it? Well...you'll have to listen to the episode.
Kaylee's 3 Sales Takeaways (No Spoilers!):
- Leverage internal executive relationships. It takes vulnerability to admit you need help but pays off in the long run.
- WIIFM (What's in it for me). Align the problems you solve with each buyer's business initiatives.
- Stay calm & trust in your champion relationship. Being creative to get a deal across the line takes guts.
Kaylee Chappelow: https://www.linkedin.com/in/kaylee-chappelow/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
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We love connecting with our listeners & always look to improve!
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 global company. How did he do it? Well...you'll have to listen to the episode.
PJ's 3 Sales Takeaways (No Spoilers!):
- Timing is everything. No amount of 'cool features' can make up for a problem you solve not being top-of-mind for the prospect.
- Don't sell them the farm right away. Focus on what needs to be solved ASAP & allow them to grow as an account later.
- Loop in the folks smarter than you in the deal early & often. Stay at the helm, but other team members shine.
PJ Ricketson: https://www.linkedin.com/in/pj-ricketson/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
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We love connecting with our listeners & always look to improve!
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 Spoilers!):
- Even in a down market, you can sell. Just need to become even more targeted & confident in your messaging.
- Team selling makes a huge difference. Don't be afraid set your ego aside & bring in your experts to help.
- There are key phrases that should perk your ears up in every deal. Know what to listen for & pounce on it.
Gerry Hill: https://www.linkedin.com/in/beaccurate/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
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We love connecting with our listeners & always look to improve!
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 uncomfortable. No problem, no sale.
- Always be prepared. Devote at least 2 hours of prospect research for every 1 hour of meeting time.
- Sell today, educate tomorrow. Get the meeting first and then educate on every problem you solve throughout the sales cycle.
Gavin Tice: https://www.linkedin.com/in/gavin-tice/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
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We love connecting with our listeners & always look to improve!
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 & transparency above all else throughout the sales process.
- Keep your pipeline full at all times. Leads from marketing & SDRs can fall through. Always prospect for yourself & have a quota backup plan.
Greg Cammarata: https://www.linkedin.com/in/gregcammarata/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
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We love connecting with our listeners & always look to improve!
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 way, especially for enterprise deals. Utilize personalize & humor whenever you can.
- Build a strong relationship with your internal Champion. It's crucial to understand their influence level.
- Stick to your guns. Your leadership may try to change course during the deal, but sell them on why the positioning you've created is best for the buyer.
Melanie LaCombe: https://www.linkedin.com/in/melanielacombe/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
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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 pipeline with a distant targeted close date? Deploy Maggie's tips on the pod today to stay top of mind & unlock the deal next stage!
Maggie's 3 Sales Tips (Summary):
- You're on your buyer's timeline: While there are always ways to create urgency; ultimately the buyer decides what's next. Follow their lead.
- No follow up, no deal: Outbound or inbound? Doesn't matter. Stay in touch consistently throughout the process & add more value.
- Always have a Champion: Of course, the decision-makers needs are important; but strong relationships with the end-users are crucial.
Connect with us!
Maggie Blume: https://www.linkedin.com/in/maggieblume/
Taylor Dahlem: https://www.linkedin.com/in/taylordahlem/
Junior Lartey: https://www.linkedin.com/in/juniorlartey/
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We love connecting with our listeners & always look to improve!
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!