Sales Talk for CEOs: From Sales Rep to CEO: Navigating the Journey to Funded Startup (Ep119)

May 14, 2024 | Sales Talk for CEOs Podcast

“It’s how you sell that becomes your differentiator in a crowded market,” explained Ross Rich. Alice was excited to talk with Ross, whom she’s known since the early days of his entrepreneurial journey. Ross, the CEO of Accord, started his company to solve a critical problem in sales: lack of transparency between teams and customers. His insights are not just about Accord’s journey from idea to successful product, but about the transformative lessons learned from evolving from a sales rep to a CEO.

Key Takeaways for CEOs:

1. The Genesis of Accord: A Lesson in Identifying Market Gaps

Ross’s journey began at Stripe, where he recognized a recurring challenge across sales teams—aligning the “why,” “how,” and “who” of deals was cumbersome and opaque. This realization spurred him to develop Accord, demonstrating the power of addressing specific market needs with precise solutions. “The whole idea behind Accord is taking those best practices that pretty much every top seller uses…and building that into software to make it really easy for both the seller and the customer to understand those three key aspects,” Ross shared.

2. Embracing the Entrepreneurial Leap: Overcoming Fear with Preparation

Ross’s transition from employee to founder wasn’t spontaneous. It was calculated and gradual, emphasizing that making ‘the leap’ should feel like a natural next step, not a risky jump into the unknown. He advised, “It shouldn’t feel like a crazy leap at the time…By the time that you’re ready to do it, it should be, hey, I have an overwhelming amount of work to do on this project.

3. The Importance of Early Customer Success Management

One of the critical early mistakes Ross acknowledged was underestimating the importance of customer success management. Before scaling the product or marketing efforts, ensuring that the initial customers are successful and well-supported is vital. This focus helps in refining the product based on real user feedback and solidifies the foundation for scaling.

What to Do Next? Actionable Steps for CEOs:

Ross’s experiences underline the necessity of not just starting a business but nurturing it through thoughtful steps and strategies. For CEOs aiming to replicate such success, here are actionable steps to consider:

  1. Evaluate Market Needs: Just as Ross identified a gap in sales transparency, CEOs should look for unmet needs in their markets that align with their expertise and business vision.
  2. Gradual Transition into Entrepreneurship: Transitioning to a full-time entrepreneurial role should be a process rather than a sudden shift. This approach reduces risk and ensures a solid foundation for the business.
  3. Prioritize Customer Success: Invest in customer success early on. This focus will not only improve your product through genuine feedback but also increase customer retention and satisfaction.

Learn all the insights Ross has to offer about enhancing your business operations by watching the full episode below.

Watch below or on our YouTube channel


[00:00] Introduction – Alice opens the episode touching on the need for CEOs to update sales strategies and the joy of reconnecting with early-stage entrepreneurs she had met.

[02:07] Welcome Ross Rick – Ross Rich, founder of Accord, joins the conversation, reminiscing about the initial connection with the show host, Alice.

[02:41] Discussing Accord – Ross introduces Accord, sharing insights from his early days as a seller at Stripe and the concept behind his company.

[03:21] Technical Interruption – A sudden audio cut forces a pause in the conversation, prompting troubleshooting efforts.

[05:43] Resuming Conversation – With technical issues resolved, they restart the discussion, focusing on Accord’s role in sales transparency and customer understanding.

[06:27] Why Accord Was Founded – Ross delves into his journey starting Accord, driven by the essentials of successful deals: the ‘why’, ‘how’, and ‘who’.

[08:03] The Genesis of Accord – Insights into the conception of Accord, Ross’s realization of an opportunity, and how he transitioned from idea to action.

[10:04] Discussing Customer Experience – Exploration of why providing a superior customer experience is pivotal in today’s competitive sales environment.

[10:53] First Steps to Entrepreneurship – Ross shares the initial hesitancies and the pivotal moment leading to the full-time commitment to Accord.

[12:15] The Importance of Customer Success – The conversation shifts to the critical role of customer success and the early challenges faced in onboarding users.

[14:27] Gaining Your First Customers – How networking and leveraging personal connections allowed Accord to acquire their initial customer base.

[16:47] Intentional Customer Targeting – Ross emphasizes the shift from an inbound marketing approach to a focused strategy on identifying and securing ideal customers.

[18:21] The Right Messaging – Continuing the marketing discussion, they explore the importance of crafting messages that resonate with the target audience.

[19:40] Building the Sales Team – Delving into sales team construction, Ross shares his advice on the timing and type of sales hires needed for a growing startup.

[21:44] Current Team Landscape – A look at Accord’s current marketing, sales, and customer success teams, and the lessons learned in building an effective go-to-market strategy.

About Guest

Ross Rich is the CEO and Co-Founder of Accord. Accord ensures rigorous deal execution by enforcing your standards for how you sell, onboard, and expand with customers. Before founding Accord Ross spent 4+ years at Stripe where he helped scale the sales team from 3 to 300+ as the top performing rep. In a past life, he worked at Columbia Records with artists such as Calvin Harris, Snoop Dogg, and Pharrell.

Social Links

Ross Rich – LinkedIn

Accord – LinkedIn

Accord – Website

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