As 2024 comes to a close, and sights set on 2025, Andrew discusses major life updates including his introduction to fatherhood, his growing and evolving consulting business, and the conclusion of How the Deal was Done Podcast plus what is on the horizon. Interested in developing business cases WITH your champions? Checkout Fluint to do just that. Grab a free download of their top performing sales frameworks and templates. And listen to a few How the Deal was Done eps by visiting: https://www.flu...
Dec 23, 2024•11 min•Season 1Ep. 59
Another special guest host episode featuring Mitchell Kasprzyk. In this episode, Dave Brock shares his unique journey into sales, highlighting the importance of understanding customer needs and building trust. He recounts memorable deal stories, particularly focusing on a young salesperson's success through effective coaching. The conversation emphasizes the significance of continuous learning and adapting sales strategies to meet customer expectations, ultimately leading to successful outcomes....
Oct 28, 2024•39 min•Season 1Ep. 58
In this episode of the Deal Stories podcast, Vince Beese, a seasoned sales leader with extensive background in sales, shares insights from his career, and focusing on a significant deal he closed with Yahoo. The highlight of this deal is navigating the RFP process, the challenges faced during negotiations, and the importance of alignment and honesty in enterprise sales. Closing it out: Vince emphasizes the need for hustle, persistence, and a clear value prop when closing large deals. Check out S...
Oct 21, 2024•19 min•Season 1Ep. 57
Chas Puleo, Senior Sales Executive at Alkami, returns to in this follow-up episode to last week's conversation (Ep. 55) to discuss the closing of a 2-year, $5 million digital banking. He highlights the importance of aligning with the client’s business needs and the role of executive involvement in moving large deals forward. Background: Chas has been a Senior Sales Executive at Alkami for five an years selling digital banking solutions to U.S. financial institutions. The $5 million deal took ove...
Sep 30, 2024•34 min•Season 1Ep. 55
Chas Puleo, a senior sales executive at Alkami, shares his experience in closing a transformative $5 million deal in the digital banking space. This episode covers the challenges of resetting a deal after a key decision-maker was promoted and the importance of business cases in complex sales cycles. Background: Chas started his career in banking and transitioned into tech sales, currently at Alkami as a senior sales executive. The deal took over two years, with an internal team evaluation for a ...
Sep 16, 2024•37 min•Season 55Ep. 1
Quick episode here. Talking a bit behind the scenes of 'how' the new Leader Leverage Podcast came to be. You can find link to the YouTube of Ep 1 of Leader Leverage Podcast below. Also, you can checkout the new Substack newsletter that goes along with it. Thanks for listening and your support! Link to Leader Leverage Podcast ep 1 now available on YouTube
Sep 09, 2024•6 min•Season 1Ep. 54
Starting by handing out flyers in grocery stores, Rob DeSantis worked his way to become a world-class seller, co-founder, and angel investor. Rob is a Co-Founder at Ariba (IPO & Acquired by SAP), early Board Member at LinkedIn, and currently a hands-on startup advisor/investor. Sales has been at the center of his success, and in this interview, Rob shares the most memorable deal and the learnings he has picked up throughout his career. For salespeople, Rob offers advice and tactics that have...
Sep 03, 2024•1 hr 18 min•Season 1Ep. 53
Check out the Full Length Episode on YouTube where Rob shares the deal stories that standout from his illustrious career so far. Questions, comments, ideas - reach out to Andrew Kappel on LinkedIn
Aug 26, 2024•4 min•Season 1Ep. 53
Mitchell Kaspryzk re-joins the podcast this time as a guest host featuring a discussion with renowned sales expert Andy Paul. Andy shares insights from his extensive career and delve into a challenging deal involving the development of real-time entertainment systems for commercial airplanes, highlighting the importance of trust and understanding in sales. Background: Andy Paul has had a long and diverse career in sales, authoring several books and hosting successful podcasts. The deal involved ...
Aug 19, 2024•33 min•Season 1Ep. 52
Ian McDonald shares a large deal, where his company first landed the initial product sale, and the process of working hard to make them into a successful multi-product and platform customer . Background: Ian McDonald is currently an AE manager at Gong with prior sales experience, at LinkedIn and CEB Ian shares a past deal including the account management tactics used to expand a customer. Background: Covers deal setup and the process and relationship development with the AE who won the new log...
Aug 12, 2024•15 min•Season 1Ep. 51
Episode 50. Thank you for listening this far. More to come! In this episode we welcome Chris Orlob who shares his boomerang journey from seller to startup founder to SaaS sales leader and now back to startup founder. For the deal we cover a recent $110,000 win for his current startup Pclub.io Background: Chris identifies more as an entrepreneur than a sales leader, having started his career at InsideSales.com and later founding startups like Conversature and Pclub.io The deal involved selling ...
Aug 05, 2024•25 min•Season 1Ep. 50
Haley Ben-Izhak shares insights into closing a significant deal with a top home care provider in the US, highlighting the challenges and strategies involved. Background: Haley Ben-Izhak is an enterprise & large account executive for Nevvon; she has a background in advertising sales, event marketing, and is also a business owner. Nevvon is an online training platform for the home care industry Challenges: Long sales cycle over two+ years Various starts and stops and executive turnover Need to...
Jul 29, 2024•21 min•Season 1Ep. 49
Caleb King, a founding Account Executive at Supered, discusses an unusual yet highly successful deal from his time at HubSpot, emphasizing the importance of recognizing and handling outliers in sales processes. The deal involved a large multinational company and was closed in just two weeks. Background: Caleb King was a channel account manager at HubSpot working with agency and consulting partners Now, Caleb also works with HubSpot partners as a Founding Account Exec at Supered. The deal involve...
Jul 22, 2024•15 min•Season 1Ep. 48
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 significant round of funding for Compyl, initiated through a first call with the CTO of a larger paren...
Jul 15, 2024•23 min•Season 1Ep. 47
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 closed a sustainability software deal with a Fortune 500 company; utilizing the Fluint one-page busin...
Jul 08, 2024•20 min•Season 1Ep. 46
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 companies, including his approach to B2B sales and marketing Adam's use of social media and content creation to driv...
Jun 24, 2024•18 min•Season 1Ep. 45
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 the world a better place. The deal involved selling a childcare benefit solution to a mid-market co...
Jun 17, 2024•35 min•Season 1Ep. 44
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 professional with over 15 years in SaaS sales, and the host of the Sales Success Stories podcast. The deal was wit...
Jun 10, 2024•26 min•Season 1Ep. 43
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 weeks by leveraging Fluint to sell compliance in the retail supply chain. Challenges: Navigating compliance r...
Jun 03, 2024•14 min•Season 1Ep. 42
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 currently serves as the CRO at Art of Mentoring. The deal involved Art of Mentoring's mentoring software platform and...
May 27, 2024•19 min•Season 1Ep. 41
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 and selling side, and was selling a cloud-based software solution. Challenges : Integrating the new so...
May 20, 2024•26 min•Season 1Ep. 40
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 mentioned in the media. Managing internal stakeholder concerns and uncertainties about the deal's feasib...
May 13, 2024•23 min•Season 1Ep. 39
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 a major media conglomerate looking to expand internationally, challenging Spreedly's existing paymen...
May 06, 2024•28 min•Season 1Ep. 38
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 services company Challenges: Failing to better understand a company’s broader culture and norms. Fa...
Apr 29, 2024•21 min•Season 1Ep. 37
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 size Challenges: Establishing trust and staying top of mind without being perceived as annoying. Adapt...
Apr 22, 2024•31 min•Season 1Ep. 36
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 for pre-medical students She secured a deal with a program director to run an academic course for M...
Apr 15, 2024•22 min•Season 1Ep. 35
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 negotiation experiences. Background: • Drew Wills transitioned from numerous roles at LinkedIn to a ...
Apr 08, 2024•27 min•Season 1Ep. 34
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 services and the importance of establishing meaningful, differentiated relationships with clients. The d...
Apr 01, 2024•23 min•Season 1Ep. 33
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. The deal discussed was with a school district, involving document management solutions, taking two y...
Mar 25, 2024•27 min•Season 1Ep. 32
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 one from earlier in his career that shaped future strategies Key Challenges: Adapting to client budge...
Mar 18, 2024•24 min•Season 1Ep. 31
