Senior Commercial Counsel

About this role

About Decagon

Decagon is the leading conversational AI platform empowering every brand to deliver concierge customer experiences.

Our technology enables industry-defining enterprises like Avis Budget Group, Block’s Cash App and Square, Chime, Oura Health, and Hunter Douglas to deploy AI agents that power personalized, deeply satisfying interactions across voice, chat, email, SMS, and every other channel.

We’re building a future where customer experiences are being redefined from support tickets and hold music to faster resolutions, richer conversations, and deeper relationships. We’re proud to be backed by world-class investors who share that vision, including a16z, Accel, Bain Capital Ventures, Coatue, and Index Ventures, along with many others.

We’re an in-office company, driven by a shared commitment to excellence and velocity. Our values — Just Get It Done, Invent What Customers Want, Winner’s Mindset, and The Polymath Principle — shape how we work and grow as a team.

About the Role

Decagon is seeking a Senior Commercial Counsel to join our dedicated, collaborative and fast-growing team. This role will serve as a senior strategic legal partner to the business, with primary responsibility for leading some of the company's most complex, high-impact, revenue-generating transactions and partnering closely with sales leadership and other senior stakeholders to structure, negotiate and close sophisticated enterprise SaaS, on-premises and strategic commercial agreements.

This role will also support broader commercial legal initiatives, including advising on strategic go-to-market models, channel programs, privacy and regulatory matters, commercial policies, maintaining and improving commercial legal templates and playbooks and partnering with cross-functional stakeholders on strategic business initiatives.

The successful candidate will be a creative and analytical thinker with exceptional business judgment who is highly detail-oriented and embraces a pragmatic, business-first approach to legal counseling. They will possess the strategic thinking, executive presence and interpersonal skills necessary to build trusted advisor relationships across the organization while remaining approachable, collaborative and solutions oriented.

The successful candidate also brings significant experience leading negotiations of complex, high-value commercial agreements with Fortune 500 and other sophisticated enterprise customers, frequently negotiating on customer paper and within highly regulated industries such as healthcare, financial services and the public sector. They are comfortable navigating novel legal and commercial issues, balancing risk with business objectives and partnering cross-functionally to help drive strategic outcomes.

This individual is an exceptional drafter and strategic negotiator, who can quickly distinguish material legal risk from negotiable issues and develop practical solutions that keep transactions moving toward successful execution. They have a proven track record of serving as a trusted advisor to business leaders, successfully managing sophisticated counterparties and mentoring attorneys while helping elevate the overall capabilities of the commercial legal team.

In this role, you will

- Lead strategy, negotiation, and execution of complex, high-value enterprise B2B agreements, including SaaS and on-premises licenses, data processing agreements (GDPR, CCPA), business associate agreements (HIPAA), information security agreements, professional services agreements, channel partner agreements, and other commercial and technology-related contracts.

- Serve as a strategic partner to sales leadership on deal structuring, risk assessment, and negotiation strategy to accelerate revenue while protecting the business.

- Partner with cross-functional teams (e.g., finance, security, support, product) to resolve complex commercial and operational issues and support new go-to-market models, pricing structures, and programs.

- Develop and improve form agreements and negotiation playbooks to drive consistency and scalability.

- Contribute to the development of workflows and processes that enable the legal team to scale effectively, including contract negotiation, execution, and tracking of contractual obligations.

- Support global expansion efforts, including go-to-market initiatives, privacy-by-design, and security-by-design programs.

- Create and deliver training to business teams on legal best practices, effective engagement with legal, and relevant legal and regulatory developments.

Your background looks something like this

- JD or equivalent U.S. law degree and active bar membership in good standing in at least one U.S. jurisdiction.

- 8+ years of commercial legal experience supporting technology companies in the SaaS industry with demonstrated experience leading complex, high-value enterprise technology transactions, including negotiations with Fortune 500 and other large enterprise customers.

- Exceptional judgment with the ability to balance legal risk and business objectives in a fast-paced, high-growth environment.

- Proven ability to build trusted relationships with senior business stakeholders and provide practical, business-oriented legal advice.

- Significant experience with AI, data protection, and privacy laws (e.g., EU AI Act, GDPR, CCPA), information security terms and technology contracting.

- Outstanding drafting, negotiation, communication, and interpersonal skills.

- Proven ability to independently manage numerous complex, business-critical matters and competing priorities.

- Demonstrated ability to improve legal processes, develop scalable contracting resources and drive operational excellence.

Even better if you have

- Recognition from sales or business teams for exceptional partnership, responsiveness and commercial judgment.

Comp: $250,000 — $300,000 + Equity

Benefits

We proudly offer the followi

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