Founding Chief of Staff Sales

About Retell AI

At Retell AI, we're not just automating calls—we’re transforming how the world communicates. Our AI voice agents are reshaping sales, support, and customer engagement for leading brands. Backed by Alt Capital, Y Combinator, and top-tier investors, we've raised $4.7M in seed funding and hit $14M ARR with just 12 people.

We’re one of the fastest-growing Voice AI startups and we're on a mission to become the standard for voice automation at scale. We're also one of the top ranking startups at https://leanaileaderboard.com/.

About the Role

As the founding Chief of Staff - Sales at Retell AI, you will define and own our enterprise sales strategy as we scale from $20M to $100M+ ARR. You will be directly responsible for closing high-value enterprise deals while building the systems, processes, and team to capture massive market demand. This is a unique, ground-floor opportunity to become Retell AI’s first sales leader, reporting directly to the CEO and shaping our go-to-market approach for years to come.

You will join a fast-moving, product-led startup with deep enterprise interest and clear product–market fit, leveraging your proven track record in scaling complex B2B enterprise sales to build lasting customer relationships and create repeatable sales motions. You will have the autonomy to run deals end-to-end, experiment with new strategies, and directly influence both our growth trajectory and our company culture. For the right candidate, there is a clear path to a VP of Sales or CRO role as our enterprise organization expands.

Key Responsibilities

• Enterprise Sales Leadership: Build the enterprise sales motion and playbook from the ground up, creating scalable processes that leverage our PLG foundation while capturing high-value enterprise deals.

• Hands-On Deal Execution: Lead complex enterprise sales cycles end-to-end, personally closing strategic deals while setting the standard for the future sales team.

• Strategic Account Development: Develop and execute targeted ABM strategies, build deep relationships with key accounts, and create repeatable processes for enterprise acquisition and expansion.

• Revenue Operations: Use CRM, analytics platforms, and AI tools to automate workflows, improve pipeline visibility, and support high-velocity growth. Align sales and customer success to ensure consistent messaging and drive upsell and cross-sell opportunities.

• Collaboration with Leadership: Partner closely with the CEO to close and expand F500 enterprise accounts, refine the enterprise GTM strategy, and deliver regular KPI reporting to the leadership team..

You Might Thrive If You

• Enterprise Sales Leadership: 7+ years of enterprise sales experience, including leadership roles, with a proven track record in scaling B2B companies from $20M to $100M+ ARR or beyond.

• Quota Achievement: Consistent attainment of ambitious sales targets and demonstrated success in closing complex enterprise deals.

• Sales Expertise: Consultative and value-based selling approach with deep familiarity with the MEDDPICC sales methodology.

• PLG to Sales-Led Experience: Background in companies that evolved from PLG to sales-led motions, operating effectively in both environments. Examples include Vercel, Carta, Ashby, Vanta, Drata, Datadog, Snowflake, Canva, Asana, or Airtable.

• Team Leadership: Proven success leading high-performing enterprise sales teams and personally closing large, complex enterprise contracts.

• Hands-On Execution: Willingness to run deals end-to-end, not just manage others.

• Enterprise Sales Process Mastery: Deep experience with consultative, multi-stakeholder enterprise sales cycles.

• Growth Mindset: Strong passion for sales with a track record of improving sales strategies, processes, and operational efficiency during rapid growth.

• Product Savvy: Ability to understand and clearly communicate the value proposition of Retell AI and related AI technologies.
  

Job Details

• Job Type: Full-time, 70 hr/week (50 hr/week onsite with flexible hours + 20 hr/week work from home)

• Cash: 220k

• Equity: 0.5%

• Commission: 80k - 180k

• Location: Redwood City, CA, US

• US Visas: Sponsors Visa & Green Card

Other Benefits

• 100% medical, dental, vision insurance coverage

• Unlimited breakfast, lunch, dinner, and snacks

• Gym and daily commute fee reimbursement

• Internet and phone bill covered

Compensation Philosophy

• Best Offer Upfront: Choose from three cash-equity balance options, no negotiation needed.

• Top 1% Talent: Above-market pay (top 5 percentile) to attract high performers.

• High Ownership: Small teams, >$1M revenue/employee, and significant equity.

• Performance-Based: Offers tied to interview performance, not experience or past salaries.

Interview Process

• Introductory Call (30 min):

Conversation with a co-founder to explore your background, sales experience, and alignment with Retell AI.

• In-Person Interviews (3 hrs):

Individual conversations with founders, including a mock discovery call simulating a real sales scenario.

• Dinner Interview (2 hrs):

Informal dinner with the founding team to get to know each other better.

• Offer:

Present offer to the selected candidate.

Learn More

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Join Retell AI to shape the future of voice automation, building scalable, impactful full-stack systems that redefine AI-driven communication.