20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI
🎯 Summary
20Sales: Sierra: Inside Silicon Valley’s Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI - Comprehensive Summary
This 67-minute episode of 20 Sales features Reggie Marable, the Head of Global Sales at Sierra (a fast-growing AI company founded by Brett Taylor and backed by Benchmark/Greenoaks). The discussion centers on Reggie’s journey, the development of Sierra’s enterprise sales machine, and the specific methodologies required to prospect, qualify, and close complex AI deals in the enterprise space.
1. Focus Area
The primary focus is Enterprise Sales Strategy and Execution within the Artificial Intelligence (AI) sector. Key themes include leadership reinvention, building a scalable sales process from the ground up in a startup environment (Series A/B stage), enterprise deal qualification (especially around AI solutions), and the critical role of deep customer partnership and technical integration.
2. Key Technical Insights
- SPEAR Sales Methodology: Sierra has formalized its sales process, moving beyond standard frameworks like MEDDIC/Challenger to create SPEAR: Strategic Partnerships, Use Case articulation, Return on Investment (ROI) justification, and Compelling execution.
- Paid Proof of Concept (POC) Model: To de-risk AI adoption and demonstrate immediate value, Sierra utilizes a paid POC where clients test the technology on specific, complex journeys. The POC investment is credited toward the long-term contract, ensuring commitment and immediate focus on measurable outcomes (e.g., containment/resolution rates).
- Forward-Deployed Engineering (FDE) Model: Sierra embeds highly technical teams (Agent Product Managers and Engineers) directly into the client engagement during the POC phase. This FDE model acts as a full-service solution, integrating deeply with client IT and business teams to ensure successful deployment and continuous agent improvement post-sale.
3. Market/Investment Angle
- Enterprise AI Sales Cycle: Enterprise AI sales cycles are long, averaging around eight months from the first meeting to closing, largely due to the need for technology deployment, trust-building, and rigorous legal/governance reviews inherent in AI adoption.
- Verticalization Strategy: Despite serving broad industries (Financial Services, Healthcare, Telecom, etc.), Sierra prioritizes verticalization in its sales structure. This allows the team to speak the customer’s language, understand specific industry trends, and craft highly relevant messaging, which is crucial for high-value enterprise deals.
- Brand Velocity: Strong customer validity and social proof (customer stories) are essential for driving velocity and potentially compressing the lengthy enterprise sales cycle.
4. Notable Companies/People
- Reggie Marable: Highlighted his career pivot from a failed CRO role (where ego hindered leadership) to joining Salesforce as a first-line leader with humility, adopting the mantra: “What are you doing for others?” (MLK Jr. quote).
- Sierra: The subject company, noted for its rapid growth, founded by Brett Taylor (praised as an “apex predator” salesperson for his ability to connect tech to business value).
- Salesforce & Slack: Mentioned as previous employers where Reggie learned the importance of not imposing a playbook but adapting strategy to the specific needs of the new organization.
- Sponsors/Mentors: Larry Shirts, Frank Filman, Danny Hertzberg, Zach Lorick, and Kevin Egan were mentioned as influential figures.
5. Regulatory/Policy Discussion
The discussion touched upon the increased scrutiny and governance required for AI deals, noting that the need for legal, compliance, and governance reviews significantly contributes to the extended sales cycle.
6. Future Implications
The conversation suggests that successful enterprise AI sales require a shift from transactional selling to deep, integrated partnership. The FDE model indicates that for complex AI solutions, the vendor must be willing to take on significant implementation risk and embed itself within the client’s operations to prove value, rather than relying on self-serve or lighter-touch models initially. The industry is moving toward requiring demonstrable ROI within the initial engagement phase.
7. Target Audience
This episode is highly valuable for Enterprise Sales Leaders, CROs, VP of Sales, Founders scaling B2B/AI SaaS companies, and Sales Operations professionals focused on complex, high-ACV outbound strategies.
Comprehensive Narrative Arc & Key Takeaways
The episode follows Reggie Marable’s journey from a significant leadership failure as a CRO to his current success building the sales engine at Sierra. The central narrative is one of humility, reinvention, and process engineering.
Reggie detailed how his initial failure taught him the necessity of putting people first and listening—a lesson he carried into Salesforce, where he accepted a demotion to rebuild his credibility. Upon joining Sierra (as employee #23), he consciously avoided importing the “Salesforce playbook,” instead synthesizing his experiences to build Sierra’s unique SPEAR methodology.
A major focus was on enterprise deal qualification and execution. Reggie stressed that multi-threading is a “team sport” requiring leadership involvement, and that in the post-pandemic environment, proving tangible ROI is non-negotiable. The paid POC, supported by the Forward-Deployed Engineering (FDE) model, is Sierra’s mechanism for de-risking AI adoption for the client while ensuring the sales team can demonstrate immediate, measurable value (Time to Value).
Finally, Reggie emphasized the relentless nature of top-tier enterprise sales, noting that he and the founders still actively prospect daily (“take out the trash”). He advocates for **craftsmanship
🏢 Companies Mentioned
💬 Key Insights
"I would say if you hire fast and you don't hire smart, you end up having to fire fast."
"What's the hardest thing for you to sustain about being a sales leader? Right now, we are in hyper-growth stage. My challenge is hiring fast, hiring smart, maintaining the awesome sales culture that we've created."
"Unacceptable reason is you're not talking to the right people, you didn't deliver value, or it was a craftsmanship issue where we didn't follow up on something, we didn't do something right, we didn't control the controllables."
"Are you delivering value? Are you solving a problem? Are you talking to the right people? Have you done your homework? Have you built business value and a return on investment for the client and see the technology they're investing in, what are they going to get out of it?"
"He says, "Good news should travel fast, bad news should travel faster." What I try to do is create an environment where people feel okay telling the truth and letting us know in advance if there's an issue so we can also jump in the boat and try to help them salvage a deal from slipping."
"When you've made a hiring mistake, what does show up? In other words, what are the signals that then ought to get fit? I was—go back to the same place I'm going to go here—craftsmanship. Craftsmanship. Yeah, craftsmanship."