Senior Manager of Contracts and Operations, Gusto

• Bachelor’s degree
• 7+ years of experience in contract management, commercial contracting, or vendor contract review and negotiation (in-house strongly preferred)
• Proven ability to take ownership of high-volume contracting pipelines and turn them into well-oiled, scalable systems
• Hands-on expertise with contract lifecycle management systems (Ironclad strongly preferred) and AI review tools (GCAI or similar)
• Demonstrated success building and improving processes, not just running them
• A builder’s mindset—hungry to experiment, optimize, and deliver measurable results
• Exceptional communication skills and the ability to influence and inspire stakeholders across legal, procurement, and the business
• A passion for showing that Commercial Legal is a driver of innovation and business impact, not a blocker
• If you’re energized by building from the ground up, pushing boundaries, and leaving a mark on how in-house legal can operate in this new AI-powered era, this role is your chance to do just that

Desirable

• We’re looking for a Senior Contracts Manager to join our growing Commercial Legal team and redefine how contracting is done at scale
• This is not a “keep the lights on” contracts role—it’s a transformational opportunity to build the contracting function of the future, powered by AI and cutting-edge process design
• In this role, you will own Gusto’s vendor contracting process end-to-end, driving contract reviews, negotiations, and approvals in partnership with Procurement, Privacy, Security, and other stakeholders while also leading the adoption of AI-driven review tools to expedite low-risk contracts
• You will set the standards, playbooks, and tooling that allow Gusto’s commercial legal function to scale with speed and intelligence as the company grows
• You’ll be the driver of innovation: determining thresholds for review, implementing smarter ways of working, and leading the way in educating our legal team—and the business at large—on new industry practices and breakthroughs in smarter contracting
• Gusto’s Legal & Compliance team partners with product teams to enable innovation, facilitate responsible company growth, accelerate the Gusto roadmap, and provide compliant products to our customers, through solution-focused counsel on legal and business risks
• We are passionate about using groundbreaking technology and excellent service to elevate the experience of small business owners and their employees. Each team member is a true owner and makes a tremendous impact every day
• The Commercial Legal team is at the forefront of that mission. We’re responsible for contracting, procurement enablement, and designing the contracting processes, playbooks, and terms frameworks that allow Gusto to grow responsibly at scale
• We combine legal judgment, process mastery, and forward-looking technology to do our jobs smarter and better every day
• You’ll be joining a team of true owners who thrive on impact—and you’ll play a critical role in taking us into the next generation of commercial legal
• Reimagine the Vendor Contracting Process
• Own Gusto’s high-volume vendor contracting pipeline—not just by reviewing and negotiating contracts, but by designing and implementing smarter processes that keep pace with a fast-growing business
• See the vendor queue as a system to optimize, using thresholds, playbooks, and tooling to separate the routine from the high-risk
• Define smart risk taking principles that balance consistency and speed, ensuring contracts move through review and approval quickly while still protecting the company
• Partner closely with Procurement, Privacy, Security, and other Third Party Risk Management stakeholders to define SLAs and deliver a process that is fast, repeatable, and scalable
• Be the AI + Tooling Pioneer
• Own and optimize Gusto’s contract review tooling, including Ironclad and GCAI, while constantly scanning the market for new technologies that can further streamline and accelerate our work
• Actively test, pilot, and recommend next-gen AI solutions, ensuring the Commercial Legal team is always on the leading edge of contracting innovation
• Design repeatable, metrics-driven workflows that make “fast, consistent, good enough” the default
• Build a metrics-first culture within the team: track, analyze, and report on how AI and smarter processes are reducing contract turn times, speeding execution, and helping Gusto meet its business goals
• Translate data into a compelling story of how Commercial Legal is not just supporting—but actively fueling company growth
• Design the Playbooks & Standards
• Develop and refine templates, playbooks, and approval flows that make our processes faster, smarter, and repeatable
• Drive efficiency across procurement and cross-functional teams by embedding scalable workflows
• Report regularly on metrics—AI adoption, cycle times, execution rates—demonstrating how Commercial Legal accelerates company goals
• Educate & Inspire
• Be the go-to educator on contracting best practices and industry innovations, especially around AI
• Lead trainings for the legal team and cross-functional partners, embedding a culture of smart, modern contracting
• Position Gusto as a model of how legal functions can scale and innovate in an AI-powered world