How the Deal was Done | Enterprise Sales Podcast

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/)

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 solution within the client's legacy systems. Navigating the complex approval processes. Key Learnings: The significance of forging strong internal alliances and understanding the client's decision-making process. The necessity of being ‘persistently pleasant ‘and resilient during prolonged sales cycles. Timestamps: (00:05:12) Introduction and Eric’s career background and journey in sales (00:08:45) Overview of the deal (00:12:30) Challenges faced during the sales process (00:16:20) Navigating internal processes (00:20:55) Competition and Strategy (00:25:40) Key learnings from the deal (00:30:15) Final thoughts and advice for sellers Resources: LinkedIn: https://www.linkedin.com/in/erichamiltonblueprint/ Book: https://www.thesalesblueprintforsuccess.com/ Instagram: EricHamiltonSalesBlueprint Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/

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 feasibility and execution. Key Learnings: Structuring deals with a detailed, proactive approach, including frequent summaries and clear next steps after discussions. Emphasize the importance of top company leaders staying close to client interactions and demos to understand customer needs and address potential challenges effectively. Timestamps: (0:01:44) Background and journey of Bion and First AML. (0:07:16) How the deal was initiated through a chance conversation at a pub. (0:10:24) Advancing through the RFP process and addressing technical requirements. (0:12:11) Importance of involving sales users and navigating internal stakeholder dynamics. (0:16:01) Overcoming challenges amid global company issues and internal concerns. (0:17:42) Learnings from structuring and negotiating large transactions effectively. Resources: LinkedIn: Bion Behdin Questions, comments, ideas - reach out to: Andrew Kappel

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 payments infrastructure; it took six months to complete with multiple team members involved in the negotiation. Challenges: Navigating a complex procurement process with stringent and unusual demands from the customer. Overcoming internal resistance and aligning multiple internal stakeholders to meet the deal's requirements and innovate on pricing models. Key learnings: The importance of aligning internal teams and stakeholders to support complex deals. The necessity of maintaining flexibility and openness in negotiations, adapting to unexpected demands and changes. Timestamps: (01:02) Meeting Shawn Curtis and the inception of a pivotal deal. (02:05) Entry into enterprise sales and initial challenges. (05:12) Crucial negotiations and internal alignments. (10:48) Strategic pivot and high-level negotiations with the media conglomerate. (16:04) Critical email and breakthrough in the deal process. (18:29) Finalizing the deal and reflecting on the arduous process. (23:18) Shawn Curtis’s insights on enterprise sales strategies and career growth. Resources: Shawn's LinkedIn RepVue | Sales Organization Ratings, Reviews, Jobs (where Shawn is the Director of Sales) Questions, comments, ideas - reach out to Andrew Kappel

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. Facing to check overconfidence when a deal seems to be made already Key learnings: Research and adapt to the corporate culture and expectations of potential clients, especially regarding dress codes. Building a strong relationship with various stakeholders, not just the primary contact, to navigate corporate dynamics effectively. Timestamps: (0:10:25) Immediate Judgment Based on Attire... Colin describes the moment his attire led to a snap judgment by the CFO. (0:13:09) Cultural Missteps and Adaptations... Colin discusses adapting to different corporate cultures. (0:13:56) East Coast vs West Coast Business Culture Differences... Insights into differing business practices between "New York" and "California" businesses and startups. (0:16:47) Building Partnerships and Networks... The importance of building networks and how past connections influence current opportunities. (0:19:23) Learning from Losses... Reflecting on how losses can be more memorable and educational than wins. Resources: Colin's LinkedIn The Nazare Wave  Episode with Ewing Gillaspy Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/Podcast Questions, comments, ideas - reach out to Andrew Kappel