About the Role:

We are looking for a highly capable and versatile leader to join the Engineering organization as an Insights & Operations (I&O) Partner. In this role, you’ll drive complex, strategic programs that span multiple teams and domains—serving as an execution partner to Engineering and Product leaders. You will create clarity from ambiguity, orchestrate collaboration across functions, and ensure the operational infrastructure of Engineering scales effectively as Gusto grows.

This is a generalist role for someone who thrives in fast-paced, high-autonomy environments and has a proven track record of delivering results on large technical programs, especially those requiring deep coordination, systems thinking, and comfort with navigating uncertainty.

About the Team:

Gusto’s Engineering organization builds the infrastructure and product capabilities that power our platform for small and medium-sized businesses. Within Engineering, the Insights & Operations (I&O) team serves as a connective tissue → working across teams, systems, and priorities to bring alignment, transparency, and momentum to our most important technical initiatives.

Here’s what you’ll do day-to-day:

Design and lead strategic and operational programs that improve execution across Gusto’s 400+ person engineering org. Own initiatives such as capital and headcount planning, operating model changes, cross-team delivery coordination, and systems that improve roadmap alignment. Serve as a trusted thought partner to senior technical leaders, helping to translate vision into systems of execution. Drive operational excellence by designing and continuously improving our team rituals, artifacts, and planning processes. Develop durable programs and decision-making frameworks to scale planning, investment, and prioritization. Build strong partnerships with teams across Product, Data, Finance, and People to ensure alignment on org-wide goals and initiatives. Apply structured problem-solving and systems thinking to ambiguous and high-impact organizational challenges. Lead projects such as: Creating a framework for how Gusto approaches monolith extraction. Standing up a coordination model for AI/ML platform initiatives. Redesigning how technical priorities are surfaced and evaluated across crafts. Manage and prepare content for executive-level forums (e.g. Engineering All Hands, QBRs, planning readouts) with a strong attention to accuracy and narrative clarity. Dive deep into technical areas when necessary to help drive alignment and unblock execution. Track and support ongoing compliance and operational requirements across the year.

Here’s what we're looking for:

6+ years of experience in technical strategy, operations, engineering program management, or chief of staff roles in fast-paced tech environments. Proven ability to drive clarity, alignment, and action across multiple teams and stakeholders. Strong systems thinker with experience designing processes that scale. Proven ability to lead cross-functional technical initiatives at scale. Strong project management skills—able to manage multiple workstreams and timelines simultaneously. Excellent written and verbal communication, including executive-facing storytelling. Confident in handling high ambiguity and in operating across technical and business domains. Excellent written and verbal communication skills, including ability to drive outcomes across leadership stakeholders. Experience with resource allocation, headcount planning, or capital investments. Nice to have: MBA and/or consulting background, previous experience in Chief of Staff-style roles, or experience in product/engineering orgs at growth-stage companies.

Our cash compensation amount for this role is between $158,300 - $195,237/year in Denver, and between $185,955 - $229,345/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.