Field sales powers the economy — but most teams are struggling. Reps are buried in admin work, managers are stretched thin, and leaders can’t see what’s really happening in the field.

Siro is redefining how field sales teams learn, perform, and win.

We started as an AI-powered coaching platform that helped reps improve their outcomes in the field.

Today, we’re something much bigger — an intelligent companion that automates sales reps’ tedious admin work, gives managers real-time visibility, and helps executives see around corners.

Our platform integrates with systems like Salesforce, analyzing thousands of in-person sales conversations to surface insights, automate workflows, and drive better outcomes across the org. Think Iron Man’s Jarvis for sales — proactive, personalized, and built directly into the tools teams already use.

Siro has raised $75M and is backed by world-class investors like Index, Fika, CRV, and SignalFire. We are trusted by leading home-improvement, retail, hospitality, and automotive brands, and powered by a lean team from Meta, McKinsey, Doordash, and Uber.

We’re building the future of human-AI collaboration in sales — and we’re just getting started.

Field sales powers the economy — but selling at enterprise scale is complex.

Contracts move slowly. Negotiations get stuck. Risk tolerance isn’t symmetrical — especially when you’re the smaller company in a Fortune 500 deal.

At Siro, we’re redefining how field sales teams learn, perform, and win — and that transformation increasingly happens inside complex commercial agreements with large customers and partners.

We’re looking for a Commercial Counsel who wants to be in the work: negotiating, drafting, redlining, and helping deals cross the line — not managing legal intake from afar.

This is a rare opportunity to join a fast-scaling AI company at the moment when legal becomes a growth accelerator, not a bottleneck.

The Role

We are hiring a Commercial Counsel to own and execute the core commercial legal work at Siro.

This is a hands-on role focused on:

• Enterprise customer contracts

• Partner and channel agreements

• Negotiations that require creativity, judgment, and pragmatism

This is not a General Counsel role.
This is not a regulatory-heavy position.
This is not a role for someone who prefers to outsource execution.

It is a role for someone who:

• Enjoys being in live deal conversations

• Thinks creatively about risk rather than defaulting to “no”

• Wants to grow with the company as volume and complexity increase

Key Responsibilities

Commercial Contract Ownership

• Lead end-to-end negotiation and execution of:

  • Enterprise customer agreements

  • Strategic partner and channel contracts

• Participate directly in customer and partner calls

• Draft, redline, and finalize agreements independently

Deal Enablement & Risk Judgment

• Balance speed, risk, and commercial reality in enterprise negotiations

• Help the business move deals forward while thoughtfully minimizing downside

• Operate effectively as the “small fish” negotiating with large enterprises

Cross-Functional Partnership

• Work closely with Sales, Partnerships, and Business Operations

• Serve as a trusted advisor to deal owners without slowing momentum

• Collaborate with external counsel (Goodwin, Pulsinelli, etc.) where specialized expertise is required — without defaulting to outsourcing core work

Product & Data Exposure (Secondary)

• Support product-related legal questions including:

  • Data privacy considerations

  • AI-driven workflows and redaction

• Partner with external specialists when needed

What We’re Looking For

Experience & Background

• 3–8+ years of legal experience, with:

  • Strong training in commercial contracts

  • Background in Big Law and/or in-house at a technology company

• Experience negotiating complex B2B or enterprise agreements

• Exposure to startup or high-growth environments preferred

Practical Legal Mindset

• Comfortable operating with ambiguity and incomplete information

• Demonstrated ability to manage risk pragmatically, not eliminate it

• Willingness to accept non-ideal terms when necessary to close strategic deals

How You Work

• Hands-on, execution-oriented, and detail-driven

• Low ego; high ownership

• Enjoys volume, repetition, and complexity — not just “big moments”

What You’re Not

• A pure regulatory or compliance specialist

• A career General Counsel looking to quarterback external firms

• Highly risk-averse or process-heavy at the expense of speed

At Siro, we are committed to creating a diverse and inclusive environment where all people feel that they are equally respected and valued, whether they are applying for an open position or working at the company. We provide equal employment opportunities to all applicants without regard to race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

Compensation Range: $170K - $270K