Head of Sales Enablement

Braintrust; United States; On-site; USD 180,000 - 260,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

Daily lunch

Flexible time off

Equity

Wifi stipend

Cellphone stipend

Job summary

Braintrust is seeking a Head of Sales Enablement to build programs that help our sales team ramp, develop, and succeed. You’ll partner with our GTM org to improve how we sell to technical teams, with a hands-on approach to coaching and development.

You’ll own onboarding, lead SDR/AE/SE training, and collaborate with Sales, Solutions Engineering, Product Marketing, and RevOps to align messaging, discovery, and value selling across complex deals.

Qualifications

• Proven track record in quota-carrying B2B sales.
• Experience in onboarding, training, or coaching.
• Ability to explain technical concepts clearly and link them to customer problems.
• Curiosity about AI and willingness to learn our product deeply.
• Strong program management and deadline prioritization.
• Builds strong cross-team relationships and uses data to improve approaches.

Responsibilities

• Own onboarding and ramp; build learning paths and milestones.
• Lead hands-on SDR/AE/SE training with leadership; use real customer scenarios.
• Coach reps on account research, pipeline creation, and complex deals.
• Coach on MEDDPICC and value selling; make coaching regular and practical.
• Collaborate with Solutions Engineering to deepen AI understanding and evaluations.
• Partner with Product Marketing on launches, positioning, and competitive training.
• Set enablement priorities using call reviews, deals, and field feedback; measure readiness.

Skills

Quota-carrying sales

Training & coaching

AI familiarity

Relationship building

Onboarding programs

Job description

About the company

Braintrust is the agent observability platform. By actively applying intelligence to agent traces and automatically surfacing the most critical patterns, Braintrust gives teams the visibility to understand how agents behave in production and the tools to improve them.

Teams at Notion, Stripe, Box, OpenAI, and Cloudflare use Braintrust to trace their agents, find the issues in their observability data, and run evals that tell them how to improve.

About the role

We’re looking for a Head of Sales Enablement to build the programs that help our sales team ramp, develop, and succeed. In this role, you’ll partner closely with our GTM org to improve how we sell to technical teams.

This is a hands-on role for someone who brings sales experience and a real commitment to developing others. Ideally, you’ve been in sales and understand how to navigate complex deals. You enjoy helping reps build those skills and can turn what you see in calls and deals into focused training and coaching.

What you will do

• Own sales onboarding and ramp. Build learning paths and practical milestones that prepare new hires to explain Braintrust’s value, lead discovery, and engage technical customers.

• Lead a hands-on training program for SDRs, AEs, and SEs, and build ongoing enablement with Sales and Solutions Engineering leaders. Use real customer scenarios, discovery and demo practice, deal reviews, and clear feedback.

• Coach reps on account research and pipeline creation through complex deal execution. Help them develop champions, build relationships across the buying team, and connect technical evaluations to a clear business case.

• Partner with frontline managers to reinforce MEDDPICC and value selling in calls and deals. Make coaching a regular part of how the team works, with practical guidance managers can use.

• Work with Solutions Engineering to develop reps’ understanding of AI and Braintrust. Help AEs and SEs run evaluations with shared customer goals, success criteria, and next steps.

• Partner with Product Marketing on product launches, positioning, and competitive training. Build and maintain decks, talk tracks, and examples that reps can find and use in customer conversations.

• Set enablement priorities using call reviews, deal outcomes, and feedback from the field. Work with RevOps and Sales leadership to measure readiness, ramp time, and conversion in the parts of the sales process you’re focused on improving.

Ideal candidate credentials

• You have a track record of success in quota-carrying B2B sales, ideally as an Account Executive selling technical products to enterprise customers.

• You have helped other sellers improve through onboarding, training, or coaching, and can explain what changed. This experience may come from an enablement role or from developing peers and new hires as a seller.

• You enjoy helping people get better at selling. You listen carefully, give specific feedback, and invest time in helping reps practice and improve.

• You are curious about AI and willing to learn our product deeply. You can explain technical concepts clearly and connect them to customer problems.

• You can build a program from an incomplete starting point, manage projects and deadlines, and prioritize as needs change. You take ownership of both the plan and the work required to deliver it.

• You build strong relationships with Sales managers and partners across teams. You seek feedback, use data to assess your work, and adapt when an approach isn’t working.

• You use AI in practical ways to support research, preparation, and learning, with good judgment about accuracy and quality.

Benefits include

• Medical, dental, and vision insurance

• Daily lunch, snacks, and beverages

• Flexible time off

• Competitive salary and equity

• Wifi & cellphone stipend

Equal opportunity

Braintrust is an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status.