Senior Manager

About the Role

We’re looking for a visionary Senior Manager, Contracts Management and Operations to lead the next evolution of how contracting happens at Gusto. This role goes far beyond contract review — it’s about re-designing how contracting happens at Gusto, using cutting-edge AI technology and systems, process design, and change leadership to create scalable, intelligent systems. 

In this role, you will own Gusto’s vendor contracting process end-to-end, while driving AI-focused transformation across contract operations. 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. If you’re energized by leading change, experimenting with new technologies, and building a model for how in-house legal teams can thrive in the AI era, this is your opportunity to make a lasting impact.

About the Team

The Legal & Compliance team partners with Gusto 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.

Here’s what you’ll do day-to-day

Lead Contract Operations Strategy

• Define and execute the long-term vision for contract management and operations, aligning process excellence, technology, and stakeholder experience.
• Drive change management initiatives that reshape how Gusto teams engage with contracts.
• Serve as the bridge between Legal, Procurement, Security, & Engineering to ensure our contracting infrastructure scales intelligently with Gusto’s growth.

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 scalable process.

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.

Pioneer AI & Digital Transformation in Contracting

• Architect and own the roadmap for contract lifecycle management (CLM), AI review tools, and data systems (we currently use Ironclad and GCAI).
• Identify, pilot, and integrate emerging technologies that automate low-risk contracts, augment legal decision-making, and ensure the Commercial Legal team is always on the leading edge of contracting innovation.

Data & Insight-Driven Culture

• Build a metrics-first culture—develop KPIs, dashboards, and insights that track contracting efficiency, risk exposure, and business impact
• Translate analytics into clear narratives that show how Commercial Legal accelerates company growth.

Team Influence & Education

• Champion change by training cross-functional partners on new tools and processes.
• Be the voice of innovation across Legal, showing what an AI-empowered legal function can achieve.
• Position Gusto as a model of how legal functions can scale and innovate in an AI-powered world.

Here’s what you’ll need for this role

• 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 and AI-powered contract review tools.
• 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.

Here’s what we’d love to see you bring to the table

• A passion for AI and technology as drivers of legal transformation.
• Experience reporting on contract repository adoption, metrics, and operational KPIs.
• Familiarity with regulated industries (e.g., financial services, payroll/tax SaaS, healthcare).
• Creative problem-solving skills and the confidence to take smart risks.
• Energy, curiosity, and a drive to be part of something groundbreaking.
• A team-first approach, with no job too big or too small.

Compensation

Our cash compensation amount for this role is between $113,190 - $133,000/year in Denver and between $132,765 - $156,000/year for New York/San Francisco. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.