How the Deal was Done | Deal Stories Podcast 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