How the Deal was Done | Deal Stories Podcast

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 Pclub's skill transformation platform to a marketing automation company for $110,000, spanning multiple departments and requiring extensive multithreading.Challenges:​Procurement demanded a significant discount, initially offering a budget far below the quoted price.​Ensuring differentiation and building a strong business case to justify the higher price point against competitors.Key learnings:​The importance of undeniable defensibility, including quantified value, differentiation, and powerful champions.​The value of a multithreaded network and having a compelling event to anchor the negotiation timeline.Timestamps:01:02 – Chris's career journey split across being a seller, leader, and entrepreneur.03:41 – Founding Conversature and its challenges.06:24 – Overview of Pclub's skill transformation platform.08:37 – How the deal started with individual subscriptions leading to enterprise interest similar to PLG model11:03 – Challenges with procurement and the negotiation process.18:48 – Key strategy for successful negotiation: undeniable defensibility.
Resources:Find Chris Orlob on LinkedInThank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpodQuestions, comments, ideas - reach out to: Andrew Kappel


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 align with the client’s budgeting periods and fit into larger software migration a la implementation of a new CRM or ERP. Key Learnings: The importance of multi-threading and engaging with multiple stakeholders early in the sales process. Using Fluint's written business case framework to improve discovery and effectively communicate the economic impact to the client. Timestamps: (0:02:46) Deal OverviewDetails and background about Hailey's company and the end-user client (0:04:25) Challenges in the DealDiscussing the hurdles faced during the sales process. (0:05:57) Integration StrategyHow Nivvon’s software integrates with the client’s systems. (0:08:24) Champion TransitionHandling the transition of the internal champion at the client’s organization. (0:14:09) Utilizing FluentThe impact of using Fluint's business case framework on the deal’s success. Resources: LinkedIn: Hailey Ben-IzhakThank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpodQuestions, comments, ideas - reach out to: Andrew Kappel

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 involved a large multinational company, closed in two weeks, and accounted for 95% of Caleb's monthly quota. Challenges: The deal followed no traditional sales or prospecting playbooks. Internal processes and demands for multiple meetings risked slowing down the deal. Key Learnings: Recognize and give special attention to outlier deals. Build a process-driven day but remain open to the unpredictability of sales. Timestamps: 00:56 – Caleb King's background and role at Supered02:59 – Overview of the whale deal from HubSpot04:13 – Selling through the channel and the unique company involved06:07 – Internal operations and managing risk for the deal08:24 – Key learnings from the deal and the importance of process09:49 – Relationship with the rev ops agency involved12:03 – Supered's go-to-market strategy and the concept of the dark funnel Resources: Find Caleb King on LinkedIn Check out Supered Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpod Questions, comments, ideas - reach out to: Andrew Kappel

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 parent organization. Challenges: The CTO's initial resistance, stating he didn't want a sales pitch and wanted to see the tool directly. Overcoming the underdog status of being a lesser-known startup in a competitive cybersecurity market. Key learnings: Demonstrating transparency and empathy can build trust even with initially resistant clients. Understanding and addressing the specific business outcomes and challenges of the client is crucial. Timestamps: 0:00:02 - Introduction and welcome 0:00:26 - Mitchell's career background 0:03:44 - Initial challenge with the CTO 0:06:11 - Networking at an industry event 0:09:34 - Developing the business case 0:15:08 - Key lessons from the deal 0:21:10 - Parallels between opera and sales Resources: Follow Mitchell Kasprzyk on LinkedIn Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpod Questions, comments, ideas - reach out to ⁠Andrew Kappel on LinkedIn

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 business case to simplify the process by aligning both internal and external stakeholders. Challenges: Selling sustainability software to buyers unfamiliar with purchasing software. Navigating the complexities of budget approval and competitive differentiation in a niche market. Key learnings: Simplifying communication and reducing friction for buyers is crucial. Leveraging relationships and industry connections can open significant opportunities. Timestamps: (0:00:00) - Background of Samantha Price (0:05:27) - Challenges in selling sustainability software (0:07:32) - Insights on understanding buyer's needs (0:10:50) - Strategies for simplifying communication (0:13:19) - Success and replication of the deal (0:14:37) - Benefits of using Fluint to create business cases with your buyers Resources: Follow Samantha Price on LinkedIn Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. Check out their solution here: ⁠fluint.io/dealpod Questions, comments, ideas - reach out to ⁠Andrew Kappel on LinkedIn

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 drive awareness and build his personal brand The importance of being adaptable and willing to iterate Adam's views on the future of sales and marketing in the B2B space Timestamps: 01:37 - Discussion on sales models and trends, including B2B vs B2C. 02:32 - Contrasting sales models for Retention.com and RB2B. 09:32 - Discussion on PLG and the feedback cycle for experiments. 11:28 - Discussion on the surprises and assumptions in the experiment. Resources: ⁠Follow Adam Robinson on LinkedIn⁠ Check out Adam's Startups: ⁠RB2B⁠ and ⁠Retention.com⁠ Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. Check out their solution here: fluint.io/dealpod Questions, comments, ideas - reach out to Andrew Kappel on LinkedIn

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 company, primarily driven by employee resource groups and the CEO. Challenges: Overcoming HR's perception that childcare wasn't a problem due to lack of direct complaints. Educating the employee resource group champion on how to present the business case effectively to executives. Key learnings: Building a strong narrative and concise business case can drive decisions from the top. Engaging and educating champions within the organization can be crucial for influencing decision-makers. Timestamps: (0:01:12) Greg’s background and entrepreneurial journey (0:04:25) Current role and responsibilities (0:06:46) Explanation of the deal and the solution provided (0:08:54) Challenges faced during the deal process (0:12:38) Importance of a strong narrative and business case (0:17:48) The final steps to closing the deal Resources: Greg's LinkedIn Greg’s podcast Fluint's top five frameworks Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. fluint.io/dealpod Questions, comments, ideas - reach out to Andrew Kappel on LinkedIn

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 with a major digital camera manufacturer and was instrumental in Scott's early career success, highlighting his innovative approach to structuring deals and leveraging company culture. Challenges: The deal faced a critical timing issue, with only days left in the fiscal year to complete the legal review and finalize the agreement. Scott had to convince internal stakeholders and navigate the client's internal processes to get the deal approved under a tight deadline. Key Learnings: The importance of a strong sales culture and rallying internal support can significantly impact the success of a deal. Building deep, personal relationships with clients and working collaboratively can lead to long-term success and substantial lifetime value for the company. Timestamps: (0:01:33) – Scott Ingram's background and career overview (0:03:30) – Introduction to the Sales Success Stories podcast (0:04:20) – The setup of Scott’s significant deal with a digital camera manufacturer (0:07:58) – Key challenges and cultural impacts during the deal (0:12:19) – Scott's critical email and the turning point in the deal (0:19:01) – Celebrating the deal and its long-term impact (0:24:17) – Conclusion and call for top sales performers to share their stories Resources:  Sales Success Media Scott on LinkedIn Scott’s Daily Sales Tip #1529 HTDWD Evan Kelsay's Top SaaS Deal Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell when they aren’t in the room. Check them out at fluint.io/dealpod Questions, comments, ideas - reach out to ⁠Andrew Kappel on LinkedIn⁠

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 requirements in the retail supply chain. Building a compelling business case that stakeholders can easily understand. Key Learnings: The importance of creating a strong, clear business case. Leveraging tools like Fluint to help you write a compelling business case can significantly speed up the sales process. Timestamps: (0:01:12) - Jarred's background and career journey (0:03:13) - Overview of SPS Commerce and Jared's role (0:03:26) - Introduction to the 50k ARR deal (0:06:04) - Typical vs. accelerated sales cycles (0:08:33) - Importance of compliance requirements Connect with Jarred Knapp on LinkedIn Thank you to Fluint for Sponsoring this episode. Fluint helps sellers build a business case that can sell for them when they aren’t in the room. Check out their solution and grab the top 5 frameworks by visiting https://www.fluint.io/dealpod Questions, comments, or future guest recommendations- reach out to Andrew Kappel on LinkedIn

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 was initiated through a referral by a key partner, targeting a large athleisure retailer with a thousand participants across two programs. Challenges: Demonstrating the capabilities of a new platform while providing access to an outdated sandbox environment. Managing complex use cases and ensuring the reassurance needed for a large-scale implementation. Key learnings: Delivering above and beyond service can differentiate and build trust with clients. Warm introductions and strong partnerships significantly ease the go-to-market challenges. Timestamps: (03:48) Bijay's background leading sellers at big orgs and now international startups plus journey to Austin (07:09) Beginning of the deal: initial contact and importance of the strategic 'thought leader' partner (08:48) Challenges faced with the sandbox environment and platform transition (10:28) Over-servicing to win the deal (13:42) Importance of reassurance and client confidence Resources: Bijay Matthew on LinkedIn Questions, comments, ideas - reach out to: [**https://www.linkedin.com/in/andrewkappel/**](https://www.linkedin.com/in/andrewkappel/)