Director Strategy Operations
Operations
New York Metropolitan Area, USA
About Leena AI
Leena AI is building the definitive AI platform for enterprise employee experience. Our flagship product, AI Colleague Studio, deploys autonomous AI colleagues that handle complex HR, IT, and finance workflows across the world's largest enterprises. Backed by top-tier investors, we grew nearly 4x last year and are rewriting the rules of how enterprises adopt AI. Our office is located in Midtown Manhattan, New York. If you want to operate at the frontier of enterprise AI – not just talk about it – this is the place.
The RoleWe're looking for a Director of Strategy & Operations to lead our central S&O function, reporting to the Chief Strategy Officer. You'll own the company's most critical cross-functional initiatives end-to-end – framing the problem, driving the analysis, shaping the recommendation, and personally landing execution alongside your peers across Sales, Marketing, Demand Gen, GTM, Product, and Professional Services.
You'll lead a team of 3 high-caliber S&O operators, setting the bar for analytical rigor, speed, and AI-native execution. Many of your initiatives will start in S&O and graduate out: when a workstream matures into steady-state operations, you'll either transition it to an existing function or hire the right operator to own it permanently – then move on to the next high-leverage problem.
This is a builder-leader role. You're in the work, not above it: shipping models, writing memos, and coding prototypes alongside your team. You'll partner with Directors, VPs, and functional leads as a peer – influencing without authority, driving alignment across orgs, and unblocking execution when others can't.
What You'll Do- Leadership's Force Multiplier: Own the CEO's and CSO's most critical strategic and operational priorities end-to-end. Frame the problem, drive the analysis, build the recommendation, and drive execution across the org – in days and weeks, not quarters.
- Build & Lead a High-Performing Team: Manage a team of 3 S&O operators. Set direction, raise the analytical and execution bar, coach on AI-native workflows, and develop a bench of talent that other functions actively want to recruit from.
- Cross-Functional Initiative Leadership: Lead initiatives spanning Sales and its sub-functions (AE, SDR, RevOps, Sales Enablement, Partnerships), Marketing, Demand Gen, GTM, Product, and Professional Services. Almost every project has cross-functional dependencies; you're accountable for navigating them and landing the outcome.
- Pricing & Commercial Strategy: Own the architecture for consumption-based pricing, platform fees, and packaging. Pressure-test the economics, model scenarios, and ship the tools (calculators, estimators, deal models) that the sales org actually uses to close.
- GTM Operations & Revenue Engine: Partner with GTM leadership to design and optimize the engine – pipeline analytics, territory planning, comp design, segmentation, forecasting, and sales enablement. When the revenue machine needs a part, your team builds it.
- Product & Professional Services Strategy: Work alongside Product and PS leadership on packaging, services attach motions, customer expansion plays, and the connective tissue between what we build, what we sell, and what we deliver.
- Incubate, Operate, Transition: Many initiatives start in S&O because no other function owns them yet. You'll stand them up, run them long enough to prove the model, then graduate them out – either by transitioning to an existing function or by hiring the steady-state owner. Scoping the role, sourcing the candidate, and setting them up to succeed is part of the job.
- AI-Native Operating System: Use LLMs, AI coding tools (Claude Code, Cursor), and automation as your default. Every member of your team operates the same way. If you need a tool, your team builds it – no tickets, no engineering dependency.
- Top-Tier Pedigree: You graduated from a top-tier institution (IIT, IIM, Ivy League, Stanford, MIT, Oxbridge, or equivalent). We care about demonstrated intellectual horsepower and the discipline it takes to get there.
- 8–12 Years of Experience: Background combining management consulting (MBB preferred), investment banking, PE/VC, and/or senior strategy and operations roles at a high-growth startup. You've led complex, cross-functional workstreams end-to-end and have a track record of measurable outcomes – not just "stakeholder-managed" them.
- People Leader: 2+ years directly managing analysts, associates, or operators. You hire well, develop talent fast, and run a small team that punches well above its weight. You raise the bar, not lower it.
- Peer to VPs: You can sit across the table from a VP of Sales, a VP of Marketing, or a VP of Product, push back where needed, build trust quickly, and drive alignment without escalating. You influence through clarity and credibility, not authority.
- Builder Mentality: You don't wait for a playbook. You see a gap, figure out the solution, ship it – and teach your team to do the same. Scrappy > polished.
- Analytically Ruthless: You can build a financial model from scratch, interrogate data until it gives you something real, and make calls under uncertainty. You're allergic to hand-wavy logic and you don't tolerate it from your team.
- AI Builder, Not Just AI User (Non-Negotiable): You don't just prompt AI – you build with it. You've shipped real things using Claude Code, Cursor, or Copilot: internal tools, automations, dashboards, prototypes. You can go from "we need a calculator for this" to a working prototype before most people finish the requirements doc. As a leader, you set this standard for your team. This is table stakes.
- Hiring Instinct: As initiatives mature out of S&O, you'll often scope and hire the steady-state owner. You should enjoy this part – defining roles, sourcing talent, and handing off cleanly.
- Communication That Cuts Through: Crisp writing. Clear thinking. You can distill a complex cross-functional problem into a one-page memo that drives an executive decision the same day.
- Work from office: This role requires you to work out of our NYC office 4 days a week.
At Leena AI, we don't just sell AI – we live it. As a Director, you set the standard for your team and shape how peer functions operate.
For this role, that means:
- Using LLMs for first-draft research, competitive analysis, deal modeling, and memos – then applying judgment to sharpen the output.
- Building internal tools, calculators, prototypes, and dashboards yourself with Claude Code, Cursor, or similar – no engineering dependency.
- Automating cross-functional operational workflows (CRM hygiene, pipeline reporting, GTM dashboards, data transforms) with AI-powered scripts and integrations.
- Holding your team to the same bar – every S&O team member is expected to be an AI builder, not just an AI user.
- Continuously experimenting – if a new tool drops that could make you or your team 2x more effective, you're trialing it that week, not that quarter.
We will rigorously evaluate your AI fluency – and your ability to develop it in others – during the interview process.