Strategy and Operations Lead

Monk is an AI-native accounts receivable (AR) platform for B2B companies, helping businesses get paid fast.

The AR stack is broken. Finance teams still chase payments with spreadsheets, reconcile AR in spreadsheets and use software that was built a decade ago. We think this is one of the largest, most ignored problems in B2B software. Trillions of dollars sit in outstanding invoices and the tools to unlock cashflow are stuck in the past. We are rebuilding Monk with AI, speed, and real craftsmanship.

We are already doing this for over $1B of accounts receivables. We are backed by leading investors and our founders bring significant experience to our company (more here).

We are early, the upside is enormous, and the hardest, but also the most rewarding work is ahead of us.

We are looking for a Strategy and Operations Lead to own Customer outcomes end to end. You will lead our deployment efforts, in partnership with Engineering and Operations. You will parachute inside a Customer's finance team and act as a thought partner/trusted advisor to their leadership. This includes everything from building out their AI strategy to building bespoke demos that match to Customer’s needs to then delivering on that strategy in close collaboration with the Customer and with our team.

You will design and ship agents that deliver on Customer’s KPIs while acting as a thought partner to our Customers.

You will build deep Customer relationships, take a consultative approach to understanding their needs, and execute alongside them. You will go deep on a Customer's billing workflows and ERP one moment, then configure and tune live agents the next.

• Act as a strategic advisor to CFOs, controllers, and AR leaders. Drive their AR strategy and make the value explicit in their language

• Own the full deployment lifecycle for a book of Customers, from scoping through go-live through ongoing optimization and expansion

• Establish yourself as a trusted advisor and expert in deploying AI to solve revenue-related challenges

• Go on-site and lead custom product demonstrations and working sessions

• Map each Customer's AR process in detail (collections, cash app, disputes, vendor portals, edge cases) and translate it into agent workflows, escalation policies, and playbooks

• Own the Customer's KPIs and report against them. Surface expansion and drive renewals off demonstrated outcomes

• Be the Customer's voice internally. Feed insights back to Engineering to shape the product roadmap

• 4+ years at a top-tier management consultancy or investment bank, or a comparable high-ownership operating role

• Exceptional communication and executive presence. You can hold the room with a CFO, CEO, and Head of Accounting

• Stellar presentation skills, including demos, slides, memos and on the spot whiteboard presentations

• Strong analytical and structured problem-solving instincts. You break ambiguous problems into solvable pieces and drive them to a number

• High agency and resilience. You own the outcome, manage scope, and do whatever it takes to make our Customers win

• Comfort getting hands-on with software and non-deterministic systems. You don't need to be an engineer, but you need to be unafraid to build, configure, and iterate

• Bias to action

• Ownership and craft: We own our work end to end and obsess over getting the details right. We believe that our Customers deserve the best possible outcomes and we strive to produce work that would get a 12/10 reaction from either our Customers or members of our team. Ownership is also knowing when to go deep on a problem and when to move fast. And when the v1 is live - we own all follow-through until it is perfect

• Speed and urgency: We ship daily. We act now. Not tomorrow and not the end of the week, but today - this hour. We love shipping fast to delight our Customers

• Radical clarity: We believe in getting to the truth. It is important that all of us reason from the same version of reality (the truth) so that we can get the best result. We strive to get the truth by any means necessary. This means being open to feedback, obsessing over improving from our mistakes and clear communication

• A broken market and a real shot at owning it. AR is huge, ignored, and ready to be rebuilt. We're early and the surface area is enormous

• $T+ market and max EV from a single AR wedge

• No clear winner has emerged in this massive category. It can be us

• Insulated from labs. This workflow is complex, too many integrations are required and the last mile in AR is too bespoke for general purpose models

• Hard problem worth solving. Revenue intelligence is challenging and inherently unsexy. Frankly, there are fewer strong companies in our space and we are building the most talent-dense team

• Undeniable $ROI that allows us to clearly illustrate value to Customers, and embeds us into integral workflows

• Our unfair advantage: We have ex-finance founders that have previously exited, scars and learnings from those experiences, an eng-first culture and late-mover advantage

• You want to be a founder someday. We are sharing everything we’ve learned building our past companies (25% of the team are 2nd time founders). One of our primary goals is to help you become a founder and create a place where you do your life’s best work (see more here)

• Real ownership and an opportunity to 10x your learning curve. You will see your work go to production and deliver results for Customers, fast. Your own experience is the greatest teacher and at Monk we are maximizing the # of times you get to have valuable experiences

• Build at the frontier of applied AI and solve hard problems. You are curious about AI and do not want to miss this moment building at the frontier

• Experienced founders that have exited before and a motivated team that is all-in

• Competitive salary and meaningful equity

• Medical/dental/vision, flexible paid time off and dinner stipend

• Beautiful office in Flatiron, New York

Category defining companies are built with exceptional people. Our team is one of the products we're shipping = come help build it.