Chief of Staff to the CTO - Engineering

Are you looking to have an impact on the daily life of millions of entrepreneurs in France (and tomorrow in Europe)?

Are you looking for a work environment that values trust, proactivity, and autonomy?

Then Pennylane is the right place for you !

Our vision

We aim to become the most beloved financial Operating System of French SMEs and Accounting Firms (and soon, European ones).

We help entrepreneurs rid themselves of time-consuming tasks related to accounting and finance while providing them with access to key financial information to assist in making the best decisions for their business.

About us

Pennylane is one of the fastest growing Fintechs in France (and soon to be in Europe!)

In 5 years of existence, we’ve managed to :

💻 Make ourselves known as a groundbreaking accounting and financial software for small businesses and their accountants

💰 Raise a total of €400 millions, including from Sequoia, the famous fund from the Silicon Valley who invested early in companies like Google, Facebook, Airbnb, Stripe, Paypal and much more...

👨‍👩‍👧‍👦 Grow from 7 cofounders to 1000 happy Pennylaners : we’re now recognized as one of the greatest places to work in France (and also remotely), with a 4.6/5 rating on Glassdoor .

🌍 Build an international environment with more than 25 nationalities, with a strong remote-friendly culture, where 30% of the employees are already working from all parts of Europe

🤝 Earn the trust of thousands of customers and accounting firms and obtain outstanding ratings

🚀 Already more than 900,000 small and medium-sized enterprises (SMEs) and over 6000 accounting firms use Pennylane in France!

In 2024, we implemented an organizational structure built around business 'tracks'. This approach integrates key stakeholders across marketing, sales, product, and customer care into unified teams focused on specific product lines or client segments. Each track operates as a mini-business, empowered with dedicated resources (e.g., product marketing, data analytics, and operational support) and direct accountability for performance.

Why this role matters at Pennylane

As Chief of Staff to the CTO, you operate as a senior leader in the Tech organisation. Your leverage does not come from managing teams but from owning the hardest problems that sit between them, and from being technical enough to earn the trust of the other engineering leaders.

You are the person the CTO trusts with ambiguous, org-wide problems. You turn that ambiguity into a clear framing, a decision, an owner and a measurable outcome.

This is not a coordination role. You are expected to have opinions on engineering strategy, staffing choices and technical trade-offs, and to defend them in front of the Tech leadership team.

Team and Context

Pennylane's Tech organisation is 70+ squads, each led by an Engineering Manager working with a PM and a Product Designer. We serve 1.5m+ customers and we want to scale in Europe. At that size, the hard problems are no longer inside a squad: how the organisation plans, how it decides, how it measures itself, how it invests in foundations without stalling product delivery. That is your perimeter.

You report directly to Quentin, Co-founder & CTO. Your influence comes from the scope of what you own and from credibility with senior engineering leaders, which is why we ask for a technical background. As the organisation grows, this role can evolve towards a management position.

Key missions

Engineering strategy and transversal initiatives

Own the strategic, cross-organization initiatives that no single squad can carry: platform or architecture programmes, reliability and quality step-changes, engineering productivity, technical debt paydown

Frame the problem, build the technical and business case, secure alignment across Engineering, Product and Security to drive execution

Lead the Tech side of company-level programmes (e.g. European expansion, major compliance or infrastructure shifts) alongside the rest of the Tech leadership

Planning & Performance tracking

Own the Tech planning cycle: collect the inputs, surface the trade-offs (capacity vs. platform, run vs. new bets), and drive the arbitration with Tech leadership

Drive the definition and calibration of Tech OKRs, and hold the organisation accountable

Define what "good" looks like for a 70+ squad engineering organization and build the metrics that measure it (delivery cadence, reliability, quality, staffing and attrition, engineering satisfaction)

Decision-making and leadership cadence

Own the Tech leadership operating system: staff meetings, QBRs, roadmap and architecture reviews. You design them, set the agenda, write or commission the pre-reads, frame the decisions to be made, and make sure decisions land

Maintain the CTO's decision log: what was decided, by whom, with what trade-off, and what happened next

Raise the quality of decision-making across the Tech leadership team

Communication

Lead internal and operational communications across the engineering organization, building clear messaging systems from board decks down to team-wide updates

Who you’ll work with?

CTO and Tech leadership (Head of Engineering / Head of Data / Senior Engineering Managers)

Rest of the leadership (CPO, VP Strategic Initiatives)

Other relevant teams (e.g. Security, Finance, People)

Who we’re looking for

Must-have

An engineering degree (engineering, computer science or equivalent scientific curriculum)

Technical fluency: you can read a design doc, follow an architecture discussion, challenge an estimate or a trade-off, and be taken seriously by senior engineers

7-10 years of experience, including significant time inside a tech organisation at scale (multiple squads, platform teams), where you have lived the problems of scaling engineering

A track record of owning complex, cross-organisational initiatives from framing to measurable outcome with senior stakeholders

Outstanding written communication: this role produces documents that senior people act on

Fluency in English

Nice-to-have

A hands-on engineering past: software engineer, engineering manager, Technical Program Manager, architect or equivalent

Experience as a Chief of Staff, VP/Director of Engineering Operations, or in a strategy & operations function inside a product-led tech company

What you can expect?

Within one month

You'll complete the company and Tech onboarding, including our application, accounting domain and engineering practices

You'll have met the Tech leadership team and formed your own view of where the organisation loses time, quality or alignment

You'll have taken ownership of the leadership cadence and the next planning milestone

Within 3-6 months

You'll be leading selected org-wide strategic initiatives end-to-end, with a measurable target

The Tech organisation will have a metrics picture it trusts and uses to make decisions

You'll be a recognised voice in the senior tech community at Pennylane, consulted on decisions rather than just informed of them

You'll be shaping the engineering narrative that the rest of the company and the board hear

Recruitment Process

- Screening interview with Barbara - Senior Recruiter (30 mins)

- An interview with Eric - VP Strategic Initiatives (1h)

- A Business Case to prepare at home and to present (1h)

- A final interview with Quentin - CTO (45 mins)

What do we do to make your work life easier

🌴 Wherever you are based, you will get 25 vacations days paid by Pennylane

💵 You’ll have a competitive compensation package

📈 You'll get company shares to enjoy a piece of the success story you're building with us

🏡 You’ll have a budget to turn your home into a more comfortable workspace, as well as a monthly allowance to work from a coworking space whenever you feel like it

⛹️ Through our partner Gymlib, you’ll have access to 8000 fitness spaces in Europe and more than 300 activ