Strategy And Operations Manager

At Trunk Tools, we’re the leading AI company revolutionizing construction, the second-largest industry on earth. We recently raised a $40M Series B led by Insight Partners, bringing our total funding to $70M from top-tier investors including Redpoint and Innovation Endeavors. This new round is fueling our next phase of growth as we scale AI agents across the jobsite.

Our mission is to build the future of construction through intelligent automation. Despite being a $13+ trillion industry, construction still runs largely on analog processes, we’re changing that by embedding AI directly into field operations.

Founded by builders and technologists (Stanford, MIT), our team has delivered software used by over 140,000 field professionals, impacting millions of users and contributing to $10B+ in built projects. Many of us come from the field ourselves, giving us a deep understanding of the industry’s unique challenges.

After years of building the “brain” of construction, we’re now launching production-ready AI agents, starting with intelligent document processing and Q&A, and rapidly expanding into core operational workflows. Our team has doubled in the past year, and with 100+ employees (50+ engineers), we’re scaling fast and entering a period of hypergrowth. This is a rare opportunity to join at an inflection point.

About the role

Trunk Tools is hiring a Strategy & Operations Manager to be a force multiplier across the entire business. You'll sit at the intersection of operations, strategy and all business functions - using frontier AI to turn manual, repeatable work into systems, and bringing sharp business judgment to the problems that matter most. This is a role for someone who is deeply AI-pilled but thinks like an operator: you'll automate what should be automated, analyze what needs analyzing, and connect the dots across functions that don't otherwise talk to each other.

This is a builder role with an outsized amount of ownership. In many ways it's a pseudo-internal PM and chief-of-staff hybrid: you'll decide what to build and fix, prioritize across functions, and ship the tooling and answers the whole org depends on. You should be extremely fluent with AI - models, tools, MCPs, automations - but you don't need to be a software engineer. The best person for this role pairs that AI fluency with genuine business sense across strategy, finance, RevOps, marketing, GTM, and broader business operations.

This is a high-leverage seat at a fast-moving, first-to-market vertical AI company: you'll be part of building the leanest, most AI-forward operating team in the space.

What you'll own

• AI-powered automation across the business: treat the company's manual workflows as a backlog. Find the repeatable, painful work across finance, ops, marketing, and GTM, and turn it into automated systems - measuring, iterating, and expanding over time.

• Cross-functional strategy & analysis: own strategic projects and analyses end to end - frame the problem, pull the data, build the answer, and drive the decision. You're as comfortable in a finance model as a marketing campaign or a GTM funnel.

• AI orchestration & enablement: be the in-house expert on applying frontier AI to real operating problems. Build lightweight agents and automations, and raise the whole team's AI capability as you go. You'll reach for LLMs, MCPs, and agents as everyday infrastructure, not novelty.

• Process & connective tissue: act as the layer that connects functions - translating messy, manual processes into repeatable systems and keeping the org running faster than its size would suggest.

What the first 90 days look like

• Stand up the first end-to-end automated workflow on the demand-gen side: signal → enrichment → scoring → routing → attribution

• Map the current manual workflows across finance, people, marketing, and GTM, and ship one or two visible automation quick wins

• Layer in the first AI-orchestration step - a lightweight agent for analysis, reporting, or supporting a specific business function

• Own one cross-functional strategic project end to end, from framing to recommendation

• Publish a prioritized roadmap of automation and operating improvements, with early wins measured against clear business outcomes

Must-have qualifications

• 4+ years of experience in a hyper-growth startup, vertical SaaS or AI-first environment, where you’ve thrived amid ambiguity, rapid change, and a high bar for execution.

• AI-pilled and fluent with the frontier - you use the latest models, tools, API calls, and MCPs daily, and you know how to turn them into working agentic automations

• Strong, broad business sense - you can dive into a problem in finance, people, marketing, or GTM, reason about tradeoffs, and figure out what actually moves the needle

• Exceptional communication - you frame problems clearly, explain your thinking crisply, and translate between technical and commercial audiences

• A builder's instinct for workflow automation and process - you go from a messy business problem to a working system fast, without waiting for a playbook

• A product mindset: able to prioritize, scope, and ship the right thing for internal "customers" across the company

• Comfort in a fast-paced, ambiguous, execution-focused environment where you own outcomes end to end

Nice-to-have qualifications

• Strategy, ops, consulting, BizOps, or RevOps background - a real plus, not a requirement

• Hands-on experience with the latest and greatest AI automation tools - Clay, Claude, ChatGPT, Zapier, and similar

• Comfort working across finance and analytical modeling

• Construction, AEC, or vertical-SaaS industry familiarity

What we offer

🎖️ A close-knit and collaborative early-stage startup environment where every voice is heard and every opinion matters

💰 Competitive salary and stock option equity packages

🏥 4 Medical Plans to choose from including 100% covered option. Plus Dental and Vision Insurance!

🤓 Learning & Growth stipend

🏠 Flexible long-term work options (remote and hybrid)

🥨 Free lunch provided in the office in NYC & Austin - you’ll never go hungry with us!

🛫 Unlimited PTO; We truly believe in work-life balance and that hard work should be balanced with time for rest and rejuvenation

🏝 IRL / In-Person retreats throughout the year

Please note: All official communication from Trunk Tools will come from an email address ending in @trunk.tools. If you receive outreach from any other domain, please disregard it or report it to us.

At Trunk Tools, we’re working hard to build a more productive and safer environment within the construction industry, and we strive to live by these same values here at Trunk Tools HQ. As an equal-opportunity employer, we are committed to building an inclusive environment where you can be you. We work hard to evaluate all employees and job applicants consistently, without regard to race, color, religion, gender, national origin, age, disability, pregnancy, gender expression or identity, sexual orientation, or any other legally protected class.