Episode 339: Crime Reporter to CRO: How Investigative Skills Drive B2B Revenue with Rebecca Grimes

GUEST: Rebecca Grimes, Chief Revenue Officer at SheerID

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In this episode of The B2B Revenue Executive Experience, Rebecca Grimes, Chief Revenue Officer at SheerID, joins host Cory Cotten-Potter to dive into her fascinating journey from crime reporter to B2B SaaS leader. Rebecca shares insights on the importance of customer obsession in driving revenue, how to effectively align sales and marketing for sustainable growth, and leveraging storytelling to create meaningful customer connections.

With more than 25 years of experience in sales and marketing, Rebecca has deep expertise in GTM strategy and a track record of driving growth for global brands through her leadership philosophy centered on creating meaningful connections between brands and their customers. She also serves as a Fundraising Committee Member for Heart Haven OutReach (H2O) and Board Advisor at Workese and Athlete Foundry, Inc.

Aligning Teams for Customer Success

Alignment across teams is the secret to sustainable growth. When marketing, sales, customer success, and revenue ops work in harmony, the entire customer lifecycle improves. It starts with defining a clear vision, understanding how each team contributes to delivering good revenue, and setting up seamless handoffs between departments to ensure consistent expectations and outcomes.

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“When we have true alignment and we center on that customer, everybody actually wins.”

Rebecca Grimes, Chief Revenue Officer at SheerID

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Healthy Revenue and Strategic Customer Segments

Healthy revenue isn't just about chasing every deal; it's about prioritizing sustainability and long-term success. This means defining what good revenue looks like, aligning with customer and business needs, and using data-driven insights to guide decisions. For example, walking from unprofitable customer segments or small deals that drain resources can free you to focus on high-value relationships that grow with your business.

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“It isn't revenue at all cost anymore. It is really healthy, good, sustainable revenue that, over time, will grow with you and position you as a strategic partner and not a vendor.”

Rebecca Grimes, Chief Revenue Officer at SheerID

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How Storytelling Drives Alignment and Connection Within Organizations

Storytelling is a vital skill for leaders, but it starts with authenticity and a deep curiosity about your customers' experiences. Leaders must actively listen, engage with customers, learn their challenges, and uncover success stories that drive connection and trust. Authentic storytelling transforms dry sales pitches into meaningful conversations, enabling leaders to build alignment, inspire confidence, and create value for both customers and teams. Sales doesn't end with a signed contract; it thrives through ongoing check-ins, regular communication, and understanding customers' evolving needs.

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“I do think that storytelling is a critical part of selling today and retaining customers. Your business champion is moving on to another company and you've got to go re-pitch and resell yourself.”

Rebecca Grimes, Chief Revenue Officer at SheerID

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Why Smarter Sales Beat Spray-and-Pray Every Time

The future of sales lies in quality over quantity, fueled by smarter use of AI tools and a deep focus on personalization. AI won't replace authentic human connections; it will enhance them by helping sales teams research prospects, understand customer needs, and uncover patterns to replicate success. It's about being smarter, focusing on winnable deals, understanding why opportunities are won or lost, and leveraging insights to position yourself effectively.

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“I think that this future is going to be one where we get smarter about placing our bets on the winnable deals and that will actually materially shift what your pipeline coverage is going to be.”

Rebecca Grimes, Chief Revenue Officer at SheerID

‍Now that you've learned Rebecca's insights on revenue leadership, discover the full list of episodes at The B2B Revenue Executive Experience. If you enjoy the show, instructions to rate and review it are found here.