Chief of Staff to the CTO - Engineering

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