Chief of Staff to the CTO - Engineering

Pennylane; Paris (KY); Remote; USD 120,000 - 180,000; Full time

Benefits offered by this job

Vacation days

Company shares

Home office budget

Gymlib access

Busuu access

Apple equipment

Remote-friendly

Job summary

Pennylane is seeking a Chief of Staff to the CTO to operate as a senior leader in the Tech organisation. You will own the hardest problems between squads, bring technical credibility, and help shape engineering strategy and staffing decisions.

You will partner with CTO and Tech leadership to drive cross‑functional initiatives, define OKRs, and improve planning, execution and alignment across 70+ squads as the company scales in Europe.

Qualifications

• An engineering degree (engineering, computer science or equivalent)
• Technical fluency: read a design doc, follow architecture discussion, challenge estimates
• 7–10 years of experience inside a tech organisation at scale
• Track record of owning complex, cross‑organisational initiatives
• Outstanding written communication
• Fluency in English

Responsibilities

• Own cross‑organization initiatives (platform, reliability, productivity)
• Frame problems, build business/technical cases, secure alignment
• Lead tech aspects of company-wide programs (e.g. European expansion)
• Define Tech OKRs and drive performance metrics
• Design and lead leadership cadence and decision processes
• Communicate clearly across the engineering org

Skills

Technical fluency

English fluency

Cross-squad influence

Strategic thinking

Strong written communication

Education

Engineering degree

Job description

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 :

• Made 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

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 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 also want to emphasize that we fully embrace diversity, equity and inclusion and that we’re doing our best to create a safe and inclusive environment.

We are committed to providing an equal employment opportunity regardless of gender, sexual orientation, origin, disabilities, or any other traits that make you who you are. If anything, diversity makes us a more fun place to work at.

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 and long‑lasting collaboration.