20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
May 2, 2025
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Reggie Marable, Head of Global Sales at Sierra and former leader at Slack and Salesforce, shares insights on navigating the fast-paced world of sales. He reflects on his early failures and the importance of humility in leadership. The discussion delves into effective sales strategies, including proof of concepts for enterprise deals and the value of verticalized sales teams. Reggie also highlights how AI tools are transforming sales efficiency, negotiating techniques for large deals, and the delicate balance of rapid hiring during hyper-growth.
Reggie Marable highlights the importance of humility and learning from failures in leadership to foster effective sales strategies.
Customizing sales methodologies like the 'PEER' framework allows teams to align their approaches with client needs and company goals.
Implementing multi-threading in sales creates deeper relationships across organizational levels, increasing the chances of closing deals successfully.
Verticalized sales teams enable stronger messaging and solution relevance by targeting industry-specific pain points for enhanced sales effectiveness.
Deep dives
Reggie's Leadership Journey
Reggie Marable reflects on his transformative leadership journey, beginning with his early career in telecommunications and a pivotal moment that led to his firing as a Chief Revenue Officer (CRO). This experience taught him the importance of humility, listening skills, and putting people first in leadership roles. After self-reflection and a significant career shift to Salesforce, Reggie adopted a more collaborative approach, which allowed him to flourish in his new position. He emphasizes that the key to successful leadership lies in being grounded, appreciative of others, and learning from past failures.
Sales Methodology Evolution
At Sierra, Reggie emphasizes the need for a flexible sales methodology tailored to the company’s growth stage and unique client needs. Drawing from his experiences at Salesforce and Slack, he successfully adapted key sales methodologies by creating a new framework known as 'PEER', which focuses on partnership, use case, ROI, and compelling events. This innovative approach helped establish a strong sales process that aligns with Sierra's objectives and optimizes sales effectiveness. Reggie argues that by actively listening and learning from each organization’s dynamics, sales leaders can customize tactics to foster success.
Importance of Multi-threading in Sales
Reggie champions the concept of multi-threading in sales, highlighting its necessity for building strong relationships with clients across various levels. He explains that having multiple contacts within an organization facilitates deeper connections and insights regarding decision-making processes. A collaborative team approach is essential to ensure that knowledge flows and the right conversations happen at critical junctures. By engaging multiple stakeholders, sales teams can create a more robust strategy that enhances their odds of closing deals.
Proof of Concept Strategy
Sierra employs a paid Proof of Concept (POC) strategy, which enables potential clients to test the technology before making long-term commitments. This low-risk approach allows organizations to evaluate the product’s efficacy while also generating initial revenue. By absorbing integration work during the POC phase, Sierra eases clients' concerns and builds their trust. Reggie notes that this model has proven successful, as they have maintained an impressive conversion rate from POCs to long-term contracts.
Verticalization in Sales Teams
Reggie advocates for building verticalized sales teams tailored to specific industries, which he believes enhances effectiveness and messaging accuracy. By concentrating on seven key sectors, Sierra ensures their sales teams can address unique client pain points and industry challenges. This approach allows representatives to speak the customers' language, grasp industry trends, and offer solutions that resonate. Reggie asserts that early implementation of verticalization is crucial for maximizing impact and establishing a strong foothold in those markets.
Building a Winning Culture
As Sierra scales rapidly, Reggie underscores the significance of maintaining a strong company culture built on trust, respect, and support. He acknowledges that amid hyper-growth, it’s vital to integrate new hires into the team effectively to ensure a cohesive environment. An open-door policy for feedback and team engagement fosters collaboration and morale. By emphasizing the importance of culture, Reggie aims to create an environment where employees are motivated to excel and contribute.
Navigating Competitive Challenges
In the competitive landscape of AI, Reggie advises founders to understand their competition while respecting their strengths. He believes that sales teams must be equipped to effectively differentiate their offerings during sales cycles. Maintaining a competitive spirit is essential, as Reggie advocates for approaching each client interaction with determination and a commitment to deliver value. This mindset not only fortifies relationships with clients but also reinforces Sierra's position in the market by showcasing their unique capabilities.
Reggie Marable is the Head of Global Sales at Sierra, a conversational AI platform for businesses. Sierra enables companies like ADT, Sonos, SiriusXM, and WeightWatchers to build AI agents that transform customer experiences. The company has rapidly become a hypergrowth leader in Silicon Valley, recently securing a funding round that values it at $4.5 billion. Before joining Sierra, Reggie was the Head of Sales in North America at Slack and the Area Vice President of Enterprise Sales at Salesforce.
In Today’s Episode We Discuss:
02:50 “What I Learned from Failing Early as a CRO”
06:06 The Most Effective Sales Strategy and the BS Sales Methodology
06:55 How to Build Sales Processes from Scratch
12:28 When and How to do Verticalised Sales Teams
14:15 How to Become World Class as Sales Prospecting and Outbound
17:21 How to Use Proof of Concepts to Win Enterprise Deals
22:04 Enterprise vs. Self-Serve: Both or One and How
30:09 Building a Sales Team from Scratch
37:39 Structuring the Hiring Process
41:14 How Founders F*** Up Hiring in Sales
46:25 Handling Salary and Title Expectations
51:36 How to Run Effective Deal Cycles
57:06:07 How to do Onboarding for New Sales Hires
59:07:48 How to do Post Mortems in Sales Processes
01:04:24 Negotiating Enterprise Deals
01:08:04 Quick Fire Round: Sales Tactics and Strategies
This episode is brought to you by Capchase, helping software and hardware companies close deals while accessing TCV upfront. Learn more at capchase.com/20vc.
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