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 Linke... more

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FAQs about How I Deal:

How many episodes does How I Deal have?

The podcast currently has 49 episodes available.

How I Deal episodes:

May 31, 2023Tanner 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!
...more
31min
April 13, 2023Jeanna 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!
...more
31min
April 05, 2023Morgan 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!
...more
31min
March 30, 2023Chris 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!
...more
30min
March 23, 2023Laura 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!
...more
32min
March 16, 2023Krysten 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!
...more
28min
March 08, 2023Cassandra 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 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!
...more
31min
March 02, 2023Justin 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. 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!
...more
35min
February 23, 2023Max 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 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!
...more
24min
February 16, 2023Christian 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!
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!
...more
27min

FAQs about How I Deal:

How many episodes does How I Deal have?

The podcast currently has 49 episodes available.