Strategy & Operations - Office of the CTO

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 https://www.glassdoor.fr/Avis/Pennylane-France-Avis-E4171708.htm. 🌍 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 https://www.google.com/search?q=pennylane&ei=O9pOYvm0Co-blwSmhKmIAw&ved=0ahUKEwi5vsWL-4H3AhWPzYUKHSZCCjEQ4dUDCA4&uact=5&oq=pennylane&gs_lcp=Cgdnd3Mtd2l6EAMyDQgAEIAEELEDEIMBEAoyCwguEIAEEMcBEK8BMgcIABCABBAKMgcIABCABBAKMgUIABCABDIFCAAQgAQyBQgAEIAEMgcIABCABBAKMgcIABCABBAKMgcIABCABBAKOgcIABBHELADOgkIABCwAxAKEEM6CgguEMcBEK8BEAo6BggAEBYQHjoICAAQFhAKEB46DQguEIAEEMcBEK8BEApKBAhBGABKBAhGGABQ7QFY6wVgugdoAXABeACAAUiIAbMCkgEBNZgBAKABAcgBCcABAQ&sclient=gws-wiz 🚀 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 The Chief of Staff to the CTO is the CTO’s “force multiplier”: they bring structure, clarity, and pace across strategy, governance, performance, and communication so the Tech organization executes faster and stays aligned Your responsibilities Governance and alignment of the Tech leadership - Structure Tech leadership rituals (staff meetings, QBRs, roadmap and tech debt reviews) and ensure they are effective (clear agenda, pre-reads, decision framing, and follow-through) - Prepare the CTO’s key messages (memos, updates, tech all-hands, executive communications) and ensure consistent narrative across audiences - Act as a facilitator both within the Tech team (with senior Engineering Managers) and with other Pennylane teams - Represent the CTO on cross-functional topics within Pennylane, including by contributing to transversal projects - Drive decision hygiene: capture decisions, owners, timelines, and ensure closure; maintain a lightweight “CTO decision log” when useful Performance & operating metrics steering - Coordinate the definition of the Tech team OKRs (definition, calibration, and alignment with company priorities) - Coordinate the Tech All-Hands in-person meetings (venue, speakers, timekeeper, Q&A) - Define, maintain, and track simple, actionable metrics (delivery, reliability, incidents, internal satisfaction, staffing, etc.) - Prepare recurring summaries (weekly, monthly) for the CTO and the leadership team - Translate key insights into clear and structured projects - Support planning cycles by structuring inputs, synthesizing trade-offs, and facilitating prioritization Strategic Tech projects management - Within the Tech team, frame, structure, and drive strategic and/or cross-team initiatives - Special projects: take ownership of high-impact projects Who we’re looking for Experience - 5+ years of experience in consulting, in a scale-up or in a fast-paced tech environment (incl. Chief of Staff or Strategic Project Manager) - Proven track record of leading complex, cross-functional initiatives - Comfortable with technical topics without necessarily being a software engineer (understanding the stakes, asking the right questions, and being able to interact with engineers) - Strong operational excellence mindset: turning strategy into cadence, decisions, and measurable outcomes - Outstanding written and verbal communication - Ability to influence without formal authority, in a demanding environment - Fluency in English and French Nice-to-have - Experience in consulting (strategy or ops), Product Ops, or Chief of Staff in a product and tech environment - Has worked with engineering teams at scale (multiple squads, platform, SRE, security) Recruitment Process - Screening interview with Orane - Senior Business Recruiter (30 mins) - An interview with Quentin - CTO (1h) - A Business Case to prepare at home and to present (1h) - A final interview with Eric - VP Strategic Initiatives (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 activities related to wellness 🇬🇧 You’ll have access to Busuu https://www.busuu.com/fr/p/start-learning?utm_medium=cpc&utm_source=google&utm_campaign=FR_FR_Web_Brand_E&utm_group=FR_FR_Web_Brand_E&utm_term=busuu&gclid=CjwKCAjw682TBhATEiwA9crl34OqnbJDliinEXFZNqOcb6391KXrgq4ZDDwEiwMdtTdtuVULvuF7HhoCgZEQAvD_BwE&gclsrc=aw.ds to perfect your English or your French 💻 You’ll get the latest Apple equipment 🏢 Depending on the teams and the requirements of the position - you'll be able to work remotely from your country of residence, as long as it is in Europe and within a maximum time difference of two hours from the CET time zone 🎉 We are committed to regularly coming together for company events such as Tech Days (which bring remote Pennylaners together every 3 months) or our annual company seminar, fostering significant moments of cohesion for everyone. If you are based in France, you will have a French contract following French regulation on top of the additional perks : 6 to 12 RTT, 5 weeks PTOs, lunch credits (Swile), Alan Blue healthcare cover and regular events in cities where Pennylaners are mostly presents (Lyon, Bordeaux, Nantes…) We're working on providing those last advantages to our people based outside of France as well, but it can be quite more complex depending on different countries. Who are we looking for ? To thrive at Pennylane, you need : -To speak English (level is assessed and appreciated according to the department you’re applying to) -To be energized by an ever-shifting work environment -To be highly collaborative (within your team or other stakeholders) -Sufficiently experienced to prioritize business-led actions on your day to day activity We know that some people are less likely to apply than others, if they don’t feel like they meet the full list of criteria. If you’re hesitating, we encourage you to apply : who knows, it might be the start of a meaningful