Head of Sales Enablement

HockeyStack is an Applied AI company on a mission to automate sales, marketing, and customer success for B2B companies. We build the most complete and accurate picture of the B2B buyer by integrating with every tool your team uses, partnering with third-party data providers, and deploying custom AI research agents. We use this data to power applications that automate high-value, high-complexity workflows across the go-to-market and revenue teams. Our core products include: Marketing Intelligence – instantly answers questions like “What led to that sudden drop in pipeline?” Account Intelligence – surfaces next-best actions to help reps move target accounts toward conversion Since launching in January 2023, we’ve come through Y Combinator, raised a $26M Series A led by Bessemer. We’re growing 3× year-over-year, have hit multimillion ARR, and process over 60 TB of GTM data monthly. Based at our San Francisco HQ, we operate fully in-person, move fast and hire people who are ready to win. Your Mission We’re hiring a Head of Sales Enablement to build and scale HockeyStack’s Sales Enablement function from the ground up with our VP of Sales . This is a rare builder’s role — you won’t just run programs, you’ll define them. You’ll create the playbooks, training, and frameworks that shape how our sales org engages with mid-market and enterprise buyers. You’ll partner closely with AEs, SDRs, and Product Marketing to make sure every rep is equipped to execute at a world-class level. What You’ll Do Build and own HockeyStack’s sales enablement strategy from scratch — designing the foundation, not just maintaining programs. Create onboarding and continuous training programs that reduce ramp time and drive measurable improvement in AE and SDR productivity. Develop and roll out playbooks, talk tracks, and competitive positioning tailored for mid-market and enterprise buyers. Partner with Product Marketing to translate messaging and product updates into tools the field can use immediately. Implement the right enablement tools, resources, and workflows to scale with a fast-growing sales org. Continuously assess performance metrics and feedback loops to identify gaps and rapidly adjust programs. Serve as the connective tissue between Product, Sales, SDR, and Product Marketing, ensuring alignment and execution against pipeline goals. What We’re Looking For 7–10+ years of experience in sales enablement, revenue operations, or sales leadership at high-growth B2B SaaS companies. Builder mindset — proven success standing up enablement programs from scratch , not just scaling existing ones. Deep understanding of mid-market and enterprise sales motions and how to enable them effectively. Strong ability to create content, processes, and training that reps actually use. Excellent facilitation, coaching, and communication skills. Based in San Francisco and able to work onsite 5 days a week . ✨ Why Join Now? We’re at an inflection point. The product is proven, the market is massive, and the opportunity is wide open. You’ll be joining a company with real traction, rapid growth, and meaningful backing—where every person still shapes the outcome. This isn’t just a job. It’s a chance to build something category-defining with people who care deeply about doing it right. As part of our San Francisco, California-based team, the on target earnings range for this role is $180,000– $240,000 USD annually , depending on experience and qualifications. HockeyStack is proud to be an Equal Opportunity Employer . We do not discriminate based on race, color, religion, sex, sexual orientation, gender identity, national origin, protected veteran status, disability, or any other legally protected status. We celebrate diversity and are committed to fostering an inclusive environment for all employees.