This is a fully remote opportunity
Gradient AI:
Gradient AI is revolutionizing Group Health and P&C insurance with AI-powered solutions that help insurers predict risk more accurately, improve profitability, and automate underwriting and claims. Our SaaS platform taps into one of the industry’s largest data lakes—tens of millions of policies and claims—to deliver deep, actionable insights. Trusted by leading carriers, MGAs, TPAs, and self-insured employers, Gradient AI has grown rapidly since our founding in 2018. Backed by $56M in Series C funding, we're scaling fast—and it's an exciting time to join the team.
About the Role:
We are seeking a Sales Enablement Manager to strengthen the connection between Marketing and Sales and ensure our teams are aligned around a consistent go-to-market strategy. In this role, you will shape the messaging, tools, and training that equip our sales team to engage prospects effectively and win business. You’ll partner closely with Marketing, Sales, and Solution Consulting to design impactful content, lead enablement initiatives, and manage our SDR team. This is a highly visible role where you’ll define how Gradient AI shows up in the market and set our sales team up for long-term success.
How you will make an impact:
- Partner with Marketing and Sales leadership to drive consistent messaging and GTM strategy.
- Design, deliver, and maintain engaging training programs and sales content that translate product capabilities and customer insights into impactful learning.
- Leverage proven frameworks such as the Challenger Sales methodology to help reps teach, tailor, and take control in customer conversations.
- Support ongoing development by equipping managers to coach effectively and holding reps accountable for continuous learning.
- Build and maintain scalable enablement resources (e.g., demo scripts, playbooks, RFP library) and ensure clear, consistent communication so reps know what to say, show, and do to win.
- Track and report on key performance indicators (KPIs) such as ramp time, rep productivity, and training engagement.
- Manage, coach, and develop the SDR team.
Skills needed to succeed:
- 7+ years of proven experience in sales enablement (required).
- Experience in both startups and more mature companies, with the ability to map where we are today to where we need to go.
- Background as a salesperson is a strong plus.
- SaaS industry experience required; insurance industry knowledge is a plus.
- Must have Salesforce experience. Salesloft and Hubspot experience is a plus.
- Client-facing experience and comfort engaging directly with customers is a plus.
- Strong people management experience, ideally with SDR or sales teams.
- Ability to quickly grasp complex business models and translate them into effective learning strategies.
- Excellent communication and presentation skills and the ability to manage multiple time sensitive projects with professionalism.
What We Offer:
- A fun, team-oriented startup culture.
- Generous stock options - we all get to own a piece of what we’re building.
- Unlimited vacation days.
- Flexible schedule that supports working from home.
- Full benefits package includes medical, dental, vision, 401k, paid paternal leave, and more.
- Ample opportunities to learn and take on new responsibilities.
We are an equal opportunity employer.
Salary Range: $140-170k base salary annually.
This role is also eligible for an annual performance bonus, equity grant, and a comprehensive benefits package. In accordance with the Massachusetts Pay Transparency Law, we are providing a good-faith salary range for this position at the time of posting. The actual salary offered will depend on the level at which the candidate is hired, as well as their experience, skills, qualifications, and location. Compensation may grow over time through merit-based increases, promotions, and company-wide adjustments. If your salary expectations fall outside this range, we still encourage you to apply so we can have a conversation.
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