This is Timefold -We’re building the future of intelligent planning—join us on the journey.

We are an AI planning optimization platform built on powerful, field-proven open-source solver technology. Simply put: we enable software builders to tackle some of the world's most complex, high-impact operational planning problems. From optimizing vehicle routing and employee scheduling to streamlining maintenance planning and field service logistics, our tech delivers massive economic value where it matters most.

We are on a relentless mission to free the world from wasteful scheduling! Founded in 2023, we represent the exciting next chapter of OptaPlanner—the legendary, field-proven open-source project that laid the foundation for everything we build today.

Today, we are a technically sharp, deeply passionate team of over 40 people. While our headquarters are nestled in the iconic Wintercircus building in Ghent, Belgium, we operate as a remote-first team with vibrant hubs across Belgium, the Czech Republic, Brazil and the US.

We're hiring a Head of Sales to own Timefold's revenue and build the commercial organisation that takes us from $3M to $10M ARR — in a market where some of the world's largest enterprises are already running our technology without ever talking to sales. If you know how to turn open-source traction into enterprise pipeline, lead a team that earns trust with technical buyers, and thrive when there's no playbook yet, we want to talk.

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About the role

As Head of Sales, you own Timefold's revenue target and the team that delivers it. You lead a team of Account Executives covering North America and EMEA, and a Revenue Operations Manager who owns the systems, data, and process infrastructure behind the commercial engine. You are responsible for the numbers, the people, and the operating rhythm that makes both sustainable.

This is a player-coach role. At Timefold's current scale, the Head of Sales is not a pure executive — they are someone who leads from the front on strategic deals, builds the commercial infrastructure, and simultaneously generates revenue. If you are looking for a large organisation to inherit, this is not the role. If you are energised by building one, it is.

You report directly to the CEO and sit on the leadership team alongside the Head of Partnerships, Head of Marketing, Head of Solutions, CTO, and CFO. You own the commercial motion; your peers own the functions that make it possible. Together you ensure Timefold goes to market as one coordinated engine.

What the role looks like day-to-day

Build the go-to-market strategy and execution engine

Define and own Timefold's go-to-market strategy: ICP prioritisation, territory design, channel mix, and the sequencing of commercial bets across geographies and segments. Be personally active in the most strategic deals — not as a last-resort escalation, but as a leader trusted by enterprise buyers who moves deals forward at the executive level

• Partner with the Head of Marketing on positioning, pipeline generation, and the account-based strategies that turn product-led interest into commercial momentum

• Develop the outbound strategy for a market where the buyer is a developer or technical leader — and where standard outbound approaches consistently underperform

• Develop and own relationships with key enterprise accounts across North America and EMEA — the logos that become the references that define Timefold's market position

• Convert Timefold's open-source presence into commercial pipeline: organisations across enterprise verticals are already using our technology. Lead the motion that turns that technical footprint into signed contracts

Own the revenue target and commercial organisation

Own Timefold's ARR target and the full commercial P&L — pipeline, bookings, revenue, and expansion.The Head of Sales builds the strategy and motion that turns that technical footprint into revenue

• Lead a team of four Account Executives covering North America and EMEA and a RevOps Manager.

• Set clear commercial targets, territory ownership, and performance expectations across the team

• Build the operating rhythm — pipeline reviews, forecast calls, deal strategy sessions, and team coaching — that drives accountability and consistent execution

• Recruit and onboard commercial talent as the team grows: define what great looks like for each role, and build the organisation to match

• Be involved in the most strategic deals — not as a last-resort escalation, but as a leader who is active in the market, trusted by enterprise buyers, and is able to move deals forward at the executive level

• Develop and owns relationships with key enterprise accounts across North America and EMEA — the logos that become the references that define Timefold's market position

• Convert Timefold's open-source presence into commercial pipeline: organisations across enterprise verticals are already using our technology.

• Lead from the front on the largest and most complex commercial opportunities, modelling the approach and standards that the AE team learns from

Lead the Sales organisation as a strategic partner to the CEO

Act as a core member of Timefold's leadership team: contribute to how the company positions itself, allocates resources, and builds toward the next stage of growth

• Own the commercial narrative in board conversations, investor reporting, and fundraising discussions — translating pipeline, bookings, and market signals into a coherent story about where Timefold is going and how it gets there

• Provide structured market intelligence to the CEO, Product, and the board: what the commercial team is seeing in the field, where deals are won and lost, how the competitive landscape is shifting, and what it means for product and strategy in collab with the RevOps Manager the Head of Sales ensures that commercial strategy is backed by data, tooling, and process.

• Help shape how Timefold earns its place as the defining scheduling optimisation platform for the builder's era — as AI raises the ceiling on what engineering teams can deliver, the demand for robust, intelligent scheduling infrastructure grows

You'll be a fit if

• Start-up energy doesn't scare you — it motivates you.

• You've built things before that didn't exist, and you'd rather own a function than inherit one.

• You have 10–15+ years of enterprise B2B sales experience, including senior sales leadership at scaling technology companies that sell to technical buyers

• You have experience scaling a company through the $3M–$20M ARR phase — ideally in a developer-led, open-source, or infrastructure product context where the commercial motion has to earn developer trust

• You are a genuine player-coach: as comfortable running a pipeline review or stepping into a strategic deal as you are setting commercial strategy and building a team

• You have led teams that sell into large enterprise organisations where engineering leadership and the CIO line hold budget — and you understand how those buying cycles actually work

• You understand the open-source-to-enterprise commercial motion: what it takes to convert technical adoption into commercial pipeline without alienating the community that created it

• You are operationally strong: you know how to build forecasting systems, pipeline discipline, and scalable sales processes that hold up as the team grows

• You work well with technically-minded founders and cross-functional peers — you bring commercial rigour without dismissing the technical instincts that built the product

• You are energised by building: teams, motions, operating rhythms, and the culture of a high-performance commercial organisation

• Experience at a Series A or early-growth company in a Head of Sales, VP Sales, or equivalent capacity is strongly preferred

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What do we offer

Culture & Environment

At Timefold, we offer more than just a paycheck; we offer a culture where you can thrive. We promise an open and authentic workplace where you will be trusted to act, trusted to ask, and supported as you seek to grow. In return, we look for people who are ready to own and deliver impactful results.

Standard Perks

• A Full Time position in a fast growing start up environment

• A competitive salary package complemented by a range of local benefits

• Flexibility to engage as an employee or independent contractor

How we work & connect

• Flexibility : our focus is on your talents, not your location. Choose the working arrangement that suits you best, whether it is remote, hybrid or on-site

• Our dedication to creating an inclusive environment, where diversity is celebrated and everyone is treated with fairness and respect <3

• Regular team building activities and gatherings to enhance (international) team spirit and cooperation (this requires a willingness to travel once or twice a year)

Department

Sales

Remote status

Fully Remote