AI Sales Enablement Strategist
AI Sales Enablement Strategist
Location: Remote / Boston, MA Employment Type: Full-Time Department: Sales / Revenue Operations
About the Role
We're looking for an AI Sales Enablement Strategist to help our sales organization work smarter. This isn't a traditional admin or ops role — it sits at the intersection of sales strategy, process design, and artificial intelligence. You'll embed with our sales team, learn how they work, identify where AI can remove friction and create leverage, and then make it happen.
You'll be part of a broader Transformation Office, working alongside a program manager and reporting directly to senior sales leadership. The people you'll interact with daily are GTM leaders, sales managers, and cross-functional teams, so you need to be as comfortable in a strategy conversation as you are evaluating an AI tool.
This role moves fast. We expect meaningful progress in the first 30 days.
What You'll Do
- Map existing sales processes end-to-end to identify where AI can create the greatest efficiency gains
- Research, evaluate, and pilot AI tools and agentic workflows that fit the team's real needs
- Act as an internal AI advocate, helping sales team members understand what's possible and building genuine buy-in
- Connect the dots between business needs and technical solutions, serving as the bridge between GTM leaders and implementation teams
- Collaborate with the Transformation Office to run structured pilots and track outcomes
- Stay current on the AI landscape, tools, use cases, and emerging capabilities relevant to sales and revenue teams
- Remove blockers and keep initiatives moving without waiting to be told what to do
What We're Looking For
Must-haves:
- Experience in or alongside a sales organization, you understand how sales teams think, what slows them down, and what motivates them
- Genuine curiosity about AI and a track record of exploring and applying new tools, even without being asked
- Strong business process instinct, you can walk into an org, quickly understand how things work, and spot where the gaps are
- Excellent communication and stakeholder skills, you can get people excited about change, not just informed about it
- Critical thinking and a bias toward action, you move fast, test ideas, and iterate
- Comfort with data, you can work with it, interpret it, and use it to make a case
Nice to haves:
- Hands-on experience with AI tools, automation platforms (Zapier, n8n, Make), or CRM integrations
- Background in management consulting, sales operations, or business development
- Familiarity with agentic AI concepts or prompt engineering
- Experience working within or alongside a formal transformation or program management structure
Who Thrives in This Role
You're not waiting for a roadmap, you're comfortable building one. You've already been experimenting with AI tools on your own, not because someone told you to, but because you're curious and you see the potential. You know how to read a room, earn trust from skeptical stakeholders, and translate technical ideas into language that resonates with business people.
You believe in the power of connecting the right tools to the right problems — and you get energy from watching a team become more capable because of something you helped put in place.
Why This Role
- Direct access to senior sales leadership and cross-functional GTM teams
- Real mandate to move fast and make an impact, not a pilot program that goes nowhere
- Support from a dedicated Transformation Office and program management structure
- Front-row seat to AI transformation in a sales context as it's actually happening