All Episodes

Displaying episodes 1 - 30 of 40 in total

Ep. 40: Exec Alignment, Surprise Onsites, and End of Quarter Plays to get the Deal featuring Eric Hamilton

In this episode, Eric Hamilton, experienced sales leader shares insights on successfully closing a $900k total contract value transaction. And how to navigate a comple...

Ep 39: Complex International Financial Services Deal with Bion Behdin, Co-Founder and CRO First AML

In this episode, Bion Behdin, Chief Revenue Officer of First AML, shares insights into winning a near million-dollar deal in the financial services and regulatory tech...

Ep. 38: Rep Boomerang 7-figure Transformation Deal featuring Shawn Curtis

Shawn Curtis shares an intense negotiation involving a high-stakes deal at Spreedly, a payments orchestration company. He discusses overcoming internal challenges, str...

Ep. 37: How the Deal Was *Not* Done, Navigating Cultural Differences with Colin Specter

Colin Specter shares his experiencing becoming the top seller at his company and a formative deal that he fell short on and what he learned from it. Background: Coli...

Ep. 36: Playing the Long Game to Win Deals, Stay Agile, and Keep Going featuring John Barrows

John Barrows, one of the top sales trainers and thought leaders, joins for a look back on his journey and fun discussion on a particularly large and memorable deal fro...

Ep.35: Selling the Vision Before Building the Product featuring Amanda Brem, Founder - The Brem Method

Amanda Brem, founder of the Brem Method, recounts how she pitched and executed her first academic coaching course for pre-medical students, overcoming skepticism and c...

Ep. 34: Bringing the Juice to Win Tough Deals featuring Drew Wills

Drew Wills shares his journey from a senior in college struggling to find a job to impressive runs at LinkedIn and Gong and now becoming VP of Sales at Brilliant. Drew...

Ep. 33 Help your Customers Win to Close Big Deals featuring Tom Cates, Founder Brookeside and Encompass- CX

Ep. #33 featuring entrepreneur Tom Cates who has a decades long career as a consultant, sales leader, and software founder. Tom got his start in sales with IBM, an MBA...

Ep. 32: Helping your customer leave a legacy to close a big deal with Donald Kelly

Donald Kelly, highlights the challenges and strategies involved in closing a large-scale deal with a school district. Kelly shares insights on the importance of acting...

Ep. 31: Avoiding POC Hell to win a $4 million enterprise deal in 10 months with Jake Dunlap

Jake Dunlap, CEO and Founder of Skaled Consulting, has worked on thousands of deals, and now he shares his expertise with organizations looking to accelerate their gro...

Ep. 30: Andrew Kappel Solo Episode - Consulting Deal Story, Audits as an Artifact, and Growth Update

In this episode Andrew shares a solo deal story from his consultancy: Benchmark Signal Consulting. Other topics mentioned- podcast growth initiatives including the new...

Ep. 29: Outcome of 7-Figure Deal: Increase in Customer Stock Price with Jesse Woodbury

Jesse Woodbury shares his journey of converting a small proof of concept into a seven-figure deal with a B2C Home Services Company. A deal so impactful it raised the b...

Ep. 28: Earth Moving Deal with Max Tipton VP, Sales - North America @ Paperless Parts

Max Tipton, VP of Sales North America for Paperless Parts, shares the story behind a transformative deal known as "The Earth Mover". Background: A pivotal deal know...

Ep. 27: Special Behind the Scenes with Host Andrew Kappel and Producer Brett Muni

In this special episode host Andrew Kappel, and producer Brett Muni reflect on some of the most popular episodes so far, explore how these lessons have impacted Andrew...

Ep. 26 Buyer and Seller Edition: $1.2M UberEats Deal with Chris Mark and Russell Bradley-Cook

In this special edition, we hear the buyer and seller perspectives on a $1.2 million deal between Uber Eats and the French startup, OCUS. Host Andrew welcomes Russell ...

Ep. 25: Expanding a Fortune 50 Account to $1.5M with Dustin Brown

Dustin Brown, a seasoned SaaS professional with over 15 years of experience, shares insights from a significant deal with a Fortune 50 company, initially a small 100-u...

Ep. 24: Closing One of the World's Largest Healthcare Companies with Jeff Kirchick

Jeff Kirchick, a seasoned software sales professional and author, relates his experience closing a significant deal with a major healthcare company. Jeff shares insigh...

Ep. 23: Winning Complex Buying Processes, a 6-figure Deal with Rachel Shi

Rachel Shi, a strategic account executive at Metadata, recounts a complex, 6-figure deal deal with a publicly traded EdTech company. Rachel has varied experience in te...

Ep. 22: Expanding a Multi-Million Dollar Fortune 200 Account with Jacob Karp

Jacob Karp, a seasoned enterprise sales expert with a dynamic background in journalism, media, public relations, and a decade in enterprise sales joins Andrew Kappel f...

Ep. 21: Special Edition Buyer & Seller Ep 7-figure deal at IBM with Ewing Gillaspy and Tito Bohrt

Want to hear a $7-figure deal story where the seller NEVER met anyone at VP or higher? Ever wonder what happens with your slides that you prepare for the champion? ...

Ep. 20: Closing a Multi-Million Dollar Deal with 100 Stakeholders with Global AE Matthew Klingner

Timestamps - (0:00:29) Matthew Klingner Intro. - (0:03:46) Matthew’s career transition and sales philosophy. - (0:06:39) Differences between transactional and enterpr...

Ep. 19: How the Deal Was Done Holiday Special Behind the Scenes

In this episode, Andrew welcomes How the Deal Was Done sponsor, Dan Currin, Co-Founder of OrgChartHub, to discuss how the deal to make this podcast was done and reflec...

Ep.18: Harnessing Board Members to Advance and Close Enterprise Sales with Jeff Kirchick

Jeff Kirchick, shares his journey and insights on a complex deal between his fintech SaaS co. and a bank. The deal involved complex buying group and multiple challenge...

Ep.17: 8-Figure Transformation Deal with former Salesforce #1 Rep Ian Koniak

Big Deal Story Alert. Ian, a former #1 enterprise account executive at Salesforce shares his journey from transactional to enterprise selling. He detailed his 8 figure...

Ep 16. Selling to the Fortune 500 as an Early Stage Startup featuring Joe Benjamin

# TIMESTAMP 1. (0:00:53) - Joe's background as early stage sales expert and multi-time founder. 2. (0:03:26) - How this deal got started through hosted event(s) 3. (0:...

Ep 15. Enterprise Deal to Pre-IPO Grocery Delivery Start-Up with Ben Richardson

In this episode of Ben Richardson shares his experience working on a big deal with an innovative pre-IPO grocery delivery company. He highlights the challenges of inte...

Ep 14. Understanding Customers to Create & Close | How the Deal and Partnership Was Done with Sean Adams

In this episode we meet Sean Adams: the head of Sales and Partnerships at Iorad. Sean brings a wealth of experience to the table. He started his career as a business o...

Ep.13: $8 Million Competitive Takeout Deal with Danny Brown

Episode with Danny Brown, a seasoned entrepreneur and CEO of AppMeetup. Danny shares valuable insights into a pivotal deal from his early business experience. What yo...

Ep.12: From selling a partnership to selling the whole company to HubSpot | How the Deal was Done with Mawghan McCabe

In this episode, we hear from Mawghan McCabe, Director Platform Partnerships at HubSpot. Mawghan shares her unique journey from her sales background in New York to wor...

Ep.11: Taking an Additive Approach to Partnership Sales with Barrett King former HubSpot Sr. Manager Global GTM Strategy

Barrett King, a partnership expert and Sr. Director, Revenue at New Breed joins to share an interesting deal story from his time as a Channel Partner Manager at HubSpo...

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