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.