Highspot is pioneering the category that is fundamentally changing the way companies increase sales productivity. On a mission to transform the way millions of people work with sales enablement, Highspot is committed to building breakthrough software with a spark of magic. We believe a great place to work is about more than the work – it’s about what the company stands for, and how it authentically represents its values in the real world. To this end, we have put intentional focus on creating equitable workspaces for each of our employees. Our goal is to create a culture where everyone feels a deep sense of belonging and is empowered to be an agent of change, with the ability to transform themselves, their workplace, and their world.

About the Role

We are seeking an accomplished, business-minded senior legal trailblazer to lead Highspot’s Commercial Legal function. As the Sr. Director, Associate General Counsel Commercial, you will report to the Chief Legal and Trust Officer and oversee a high-impact team. You will drive global customer and partner deal execution, shape commercial legal strategy, and act as a key strategic advisor to our go-to-market teams and C-suite executives, directly influencing Highspot's growth in the competitive sales enablement market.

In this highly visible role, you'll impact Highspot's growth by enabling Fortune 500 deals and building scalable legal frameworks - perfect for a pragmatic leader who balances executive counsel with hands-on negotiation when needed to close critical deals.

What You'll Do

Serve as a trusted legal and business advisor to Sales, Services, Deal Desk, RevOps, Finance, and other cross-functional leaders, building strong relationships and effectively managing difficult conversations to drive business outcomes while mitigating legal risk.
Negotiate, draft, and approve complex outbound SaaS agreements, including enterprise deals, strategic partnerships, and reseller, and data processing agreements.
Oversee legal support for inbound procurement, vendor agreements, and Highspot’s partner program.
Represent Legal in sales forecasting and planning meetings, and bring a legal lens to product launches, pricing, packaging, and go-to-market strategy.
Lead a high-performing team of commercial attorneys and legal professionals through effective coaching, knowledge sharing, and career development, while managing escalations and creating opportunities for professional growth.
Drive legal operations initiatives, including template standardization, metrics and KPIs, workflow design, and CLM/tool implementation.
Partner closely with Privacy, Security, and Product teams on matters involving data protection, AI, and compliance.
Collaborate on process improvements that support scale, efficiency, and high-velocity deal execution.

Your Background

J.D. from an accredited law school and active license to practice law in the U.S.
15+ years of relevant legal experience, including extensive in-house work at a high-growth SaaS company.
Deep expertise in commercial transactions, SaaS, revenue recognition, data privacy (including GDPR/CCPA/DPA frameworks), security, tax, intellectual property, and artificial intelligence.
Strong understanding of commercial metrics, legal KPIs, and how legal teams support Sales and RevOps success.
Demonstrated success building and leading high-performing commercial legal teams, with a track record of developing talent, influencing cross-functional stakeholders, and handling executive-level negotiations in complex enterprise deals.
Experience implementing or enhancing legal operations tools and processes (e.g., CLM, playbooks, metrics dashboards).
Exceptional interpersonal skills with a proven ability to communicate effectively across all levels of the organization, remain composed during high-pressure negotiations, deliver difficult messages constructively, and operate with integrity and good judgment in ambiguous situations.
Passionate about tackling novel legal issues with a proactive, business-oriented mindset, where your work directly enables Highspot's mission to transform how companies drive revenue through sales enablement.

Base salary range: $261,739 - $340,000

Employees may also be eligible for bonuses, stock options, and other forms of compensation.

The above represents total expected compensation for this role. Actual compensation will depend on various job-related factors, including, but not limited to, location, experience, and job qualifications.

Highspot also offers the following employee benefits for this position:

-Comprehensive medical, dental, vision, disability, and life benefits

-Health Savings Account (HSA) with employer contribution

-401(k) Matching with immediate vesting on employer match

-Flexible PTO

-8 paid holidays and 5 paid days for Annual Holiday Week

-Quarterly Recharge Fridays (paid days off for mental health recharge)

-18 weeks paid parental leave

-Access to Coaches and Therapists through Modern Health

-2 volunteer days per year

-Commuting benefits

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Equal Opportunity Statement

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of age, ancestry, citizenship, color, ethnicity, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or invisible disability status, political affiliation, veteran status, race, religion, or sexual orientation.

Did you read the requirements as a checklist and not tick every box? Don't rule yourself out! If this role resonates with you, hit the ‘apply’ button.

Apply now

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