How the Deal was Done | Deal Stories Podcast

Mitchell Kasprzyk, VP of Sales at Compyl, shares a pivotal deal story that led to a significant funding round for his organization. His journey from opera singer to sales leader adds a unique twist to his approach and philosophy in selling. Background: Mitchell Kasprzyk started his career as an opera singer before transitioning to sales, now serving as VP of Sales at Compyl. The deal involved a si...

Samantha Price shares her career journey from journalism to sales and details a recent significant deal she closed at Persefoni. She highlights the unique challenges of selling sustainability software to Fortune 500 companies and the strategies she uses to succeed. Background: Samantha transitioned from journalism to sales and now works at Persefoni, focusing on environmental sustainability. She c...

Welcome to a special, non-traditional episode with founder Adam Robinson. His perspectives around organic/social marketing and product lead growth (PLG) have guided the success of his software startups. B2B sellers may learn techniques from Adam's approach to improve his companies' prospecting and sales process execution. Key Topics: Adam's experience with building and growing his comp...

Greg Crisci discusses his unique approach to selling childcare benefits to enterprises, emphasizing the importance of storytelling and business cases. He shares a notable deal that took over 400 days to close, highlighting the challenges and key learnings from the process. Background: Greg is an entrepreneur at heart with a history in startups and a focus on selling products and services that make...

In this episode, Scott Ingram shares his journey through a significant sales deal that not only secured a world-class client but also exemplified the power of teamwork and cultural values. Scott's experience emphasizes the importance of perseverance, client relationships, and leveraging company culture to achieve remarkable sales success. Background: Scott Ingram is a seasoned sales profession...

In this episode of "How the Deal Was Done," Jarred Knapp, an enterprise AE at SPS Commerce, shares his journey from kinesiology to sales success. He details closing a 50k ARR deal in just three weeks using Fluint to build a strong business case. Background: Jarred Knapp transitioned from kinesiology to sales and has been with SPS Commerce for nine years. He closed a 50k ARR deal in three...

In this episode of "How the Deal Was Done," Andrew Kappel and Bijay Alex Mathew discuss a major deal with a leading athleisure retailer facilitated through a key partnership. They explore the challenges faced with outdated software and how over-servicing and strong partnerships played a role in closing the deal. Background: Bijay has 20 years of experience leading sales teams and current...

In this episode, Eric Hamilton, experienced sales leader shares insights on successfully closing a $900k total contract value transaction. And how to navigate a complex deal in the tech industry, emphasizing the importance of customer-centric strategies and teamwork. Background : The deal involved an automotive company, took six months to complete, involved multiple stakeholders from the buying an...

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 sector. Bion highlights the importance of strategic client engagement, internal stakeholder management, and leveraging feedback loops to navigate complex sales processes. Challenges: Securing buy-in amidst global company issues ment...

Shawn Curtis shares an intense negotiation involving a high-stakes deal at Spreedly, a payments orchestration company. He discusses overcoming internal challenges, strategic decision-making, and lessons learned from pivotal career transitions. Background: Shawn Curtis transitioned from a U.S. Navy career to sales, eventually becoming the first enterprise salesperson at Spreedly. The deal involved...

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: Colin Specter started his career in SaaS sales at Namely where he became a top 1% seller and progressed to a leadership role now at Orum. The deal involved namely, a tech company specializing in HR software, to the CFO of a large financial...

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 from his time at Thrive Networks. Background: John Barrows has 20+ years of sales experience with a variety of companies and as an entrepreneur In this episode he remembers a managed IT services deal he did that was 20x the avg. deal si...

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 challenges along the way. Through determination and leveraging her strengths, she successfully built a thriving business despite initial uncertainties. Background: Amanda Brem founded the Brem Method, specializing in academic coaching...

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 emphasizes the importance of networking, leveraging LinkedIn, and sales negotiations. The podcast highlights Drew's approach to renewing a significant deal with a customer by demonstrating indispensable value and learning from past...

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 from Wharton, moving into management consulting, and eventually starting his own consulting firm and software company focused on B2B business relationships. Background: Tom shares insights on selling high-value B2B products and serv...

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 as a consultant rather than an order taker and the lessons learned from navigating a complex sales process. Background : Donald Kelly transitioned from various sales roles into the founder of a sales training firm and podcast host....

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 growth. In this episode he recounts a three part deal that grew to $4M in ten months and the sales strategies and philosophies to get there. Background: Jake Dunlap is CEO Skaled Consulting. Has worked on thousands of deals and shares o...

In this episode Andrew shares a solo deal story from his consultancy: Benchmark Signal Consulting. Other topics mentioned- podcast growth initiatives including the new YouTube channel and some big upcoming guests. Resources mentioned: https://perell.com/essay/imitate-then-innovate/ Episodes Referenced: https://www.dealstoriespodcast.com/episodes/ep-21-special-edition-buyer-se YouTube: https://www....

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 buying company’s share price. This deal is a perfect example of the power of internal champions and genuine customer relationships. Background on Jesse and the deal: Jesse Woodbury is a seasoned sales professional and Sales Players po...

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 known as "The Earth Mover." The deal was with a major custom part manufacturer in the U.S., aiming to revolutionize their estimation and quoting process. This opportunity was significant for Paperless Parts, marking a st...

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's Sales Consulting Business, and enlist the audience to connect with us on LinkedIn to let us know what content has been the most engaging. Timestamps: 0:01:54 - Discussion on the podcast journey and the milestone of 25 episodes...

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 Bradley-Cook from HubSpot and Chris Mark, a tech strategy operations expert, to share their firsthand experiences and learnings from this transformative deal. Background : The deal was $1.2m between Uber Eats and OCUS, a French start...

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-user engagement that he expanded to over 1,200 users. Background: Dustin: 15+ years in SaaS, transitioned from small business digital marketing to SaaS platforms. Deal Context: Major deal with a Fortune 50 company, formerly part of De...

Jeff Kirchick, a seasoned software sales professional and author, relates his experience closing a significant deal with a major healthcare company. Jeff shares insights on the importance of relationship-building, understanding customer needs, and strategic partnerships in the sales process. Timestamps: 0:00: Introduction by Andrew 1:00: Jeff Kirchick joins and introduces himself 2:15: Jeff discus...

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 tech sales, having worked in various roles and organizations, including Hootsuite and Vidyard, and even founding her own startup. Background: Rachel is a Strategic Account Executive at Metadata, with a background in design, founding a...