Head of Sales Enablement

About Adaptive:
Adaptive is a cybersecurity startup on a mission to stop AI-powered cyberattacks, founded by Brian Long and Andrew Jones—proven entrepreneurs behind Attentive (Forbes Cloud 100, $10B+ valuation) and TapCommerce (acquired by Twitter). In April 2025, Adaptive raised $43M, led by a16z and the OpenAI Fund, marking OpenAI's first-ever cybersecurity investment.

As generative AI drives new cyber threats, Adaptive is building the defense layer every organization needs. Our platform combines personalized security training, AI-driven attack simulations, and automated threat triage, all powered by the Adaptive Risk Intelligence Engine to quantify human risk at the individual level. Trusted by top banks, tech companies, and healthcare organizations, we protect teams from emerging threats like deepfakes, smishing, and voice scams. With a solid product foundation and a $200B+ market to transform, we're just getting started.

The Role
We’re hiring a Head of Sales Enablement to build and lead the function from the ground up. Based in our San Francisco HQ, you’ll be responsible for arming our go-to-market teams with the content, tools, training, and systems they need to close large, complex deals with speed and confidence.

You’ll work closely with Sales Leadership, Marketing, Product, and RevOps to build scalable onboarding, craft compelling messaging, and ensure every AE and BDR can consistently execute a world-class sales process.

This is a strategic, high-leverage role that directly impacts our ability to scale revenue efficiently and win in the enterprise.

What You’ll Do

• Build Adaptive’s sales enablement function from the ground up—strategy, playbooks, training, and content

• Design and execute onboarding and ongoing development programs for AEs and BDRs

• Develop scalable resources (decks, one-pagers, competitive battlecards, talk tracks, objection handling) that elevate rep effectiveness

• Partner with Sales Leadership to identify skill gaps and design targeted coaching initiatives

• Work with Product Marketing to translate features into value-driven messaging and narratives

• Own enablement KPIs: time-to-productivity, win rates, average deal size, sales cycle velocity

• Help implement and optimize tools and systems that support rep productivity and knowledge retention

• Act as the connective tissue across Product, Marketing, and Sales to ensure tight alignment and GTM execution
  

Who You Are

• 6–10+ years of experience in B2B sales enablement, revenue enablement, or GTM operations

• Strong track record enabling high-performing sales teams in a fast-paced SaaS environment

• Deep understanding of enterprise B2B sales cycles and how to support reps through them

• World-class communicator with an ability to distill complexity into clarity

• Highly collaborative, resourceful, and proactive—you build systems that scale

• Experience building enablement functions from scratch is a major plus

• Comfortable working in-office in San Francisco
  

What We Offer

• A leadership role in one of the most innovative cybersecurity companies in the world

• Equity in a venture-backed business led by repeat founders

• Premium healthcare and wellness benefits

• Tight-knit team culture built on speed, ownership, and creativity

• A front-row seat to scaling a high-growth, category-defining company