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:

August 31, 2022CJ 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 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
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
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29min
August 24, 2022Cam 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 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!
...more
25min
August 17, 2022Lesley 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 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/
Help us out!
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
...more
28min
August 10, 2022Bradley 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 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/
Help us out!
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
...more
27min
August 03, 2022Spencer 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 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/
Help us out!
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
...more
26min
July 28, 2022Ricky 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 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/
Help us out!
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
...more
41min
July 20, 2022Amy 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 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/
Help us out!
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
...more
28min
July 13, 2022Nick 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). 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/
Help us out!
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
...more
28min
July 07, 2022Amelia 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 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/
Help us out!
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
...more
19min
June 29, 2022Taylor 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 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/
Help us out!
Enjoying our conversations? Consider leaving a rating & review for the show.
We love connecting with our listeners & always look to improve!
...more
21min

FAQs about How I Deal:

How many episodes does How I Deal have?

The podcast currently has 49 episodes available.