49 episodes

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.

How I Deal Taylor Dahlem

    • Business
    • 5.0 • 12 Ratings

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.

    Tanner Lacey @ Sales Assembly (#49)

    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 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!

    • 30 min
    Jeanna Humble @ Gamify (#48)

    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. 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!

    • 30 min
    Morgan Buchanan @ Spekit (#47)

    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 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!

    • 30 min
    Chris Horton @ Workstream (#46)

    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. 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!

    • 29 min
    Laura Erdem @ Dreamdata (#45)

    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 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!

    • 31 min
    Krysten Conner @ UserGems (#44)

    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 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!

    • 27 min

Customer Reviews

5.0 out of 5
12 Ratings

12 Ratings

ataylor home service ,

Amazing topics, guest and AWESOME hosts!!

Such a fan of what ALL this podcast entails- learnings and take-aways from each episode 🙌🏼

brando_nelson ,

Love it!

Awesome podcast. Both Junior & Taylor are very real and authentic. I got a lot of great ideas from listening to them. They discuss and dive deep into real scenarios that are very applicable to anyone in sales. Excited for more episodes to come!

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