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@john:matrix.john-reynolds.com

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https://www.linkedin.com/in/john-reynolds-74511660/

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Hey you 👋 Welcome to my CV! Feel free to click around, if you’re feeling brave you could even leave questions/comments! Want some more detail about me as a person and how I am to work with? Check out my About Me page!

👨‍💻 What I want next

I’m obsessed with being part of building the perfect internal technology function at organisations and it’s a journey I feel is far from done. I’ve built from scratch, reinvented existing teams and seen everything from 80 to 2000 person companies. I want to consolidate what I’ve learned across these journeys and help build an “internal tech” function that covers IT functions, HR systems, Finance and GTM systems with an alarmingly small and breathtakingly effective team of experts.

💭 What I know

📈 High-growth environments

I’ve worked across multiple unicorns and start/scale ups in all forms. From first-100 solo IT gigs through to IPO readiness and governance at 2000+ headcount and moving between those quickly, including direct experience of 10x headcount growth (100 ⇒ 1000) inside of 24 months.

🤲 Modern SaaS platforms and using them together

Extensive experience with Google Workspace, Slack, Okta, Notion and everything “startup stack” along with the technologies, standards and APIs that can tie them together. I live and breath the interstitial technologies of a modern tech company.

⚡ Automation-first approaches

Servicing an outsized user base with a small team by leaning into technology not people to fix problems. I strongly believe and have seen 1000 person companies served by mind-blowingly small and productive teams of 3 by building with automation at the heart of every decision.

🧑‍🤝‍🧑 World-class, enabled teams

Huge breadth of experience both with greenfield team building from the ground up and reinvigorating existing teams into world-class functions outperforming entire departments. I’ve helped juniors become managers or staff-level experts and I pride myself on the culture I can help instill whether from leading or building alongside the team.

🔧 Supporting anything, everything and everyone

I’ve bootstrapped teams on tight budgets and worked in managed service providers where we need to work with what we have not what we want. The core goal remains the same which is always to build a delightful function and a productive, unblocked workforce.

✨ Making a support function that isn't a chore

One of my greatest points of pride is building a support team that the rest of the company genuinely enjoys using. Where getting help isn't something that induces dread and every interaction leaves the person happier and more productive with long-term, genuine solutions over break-fix cycles and layers of help desk bureaucracy.

📖 Applying what I know anywhere

I’ve taken experience with scaling and automating in a lean team and applied to new situations and contexts. Every modern knowledge-based workflow can be improved with an eye on automation and building knowledge within a small team to have an outsized impact. Where my roots are forever in IT I’ve applied this far beyond solely that field.

🔍 The technical detail

I know my way around all of the required parts to build an internal tech function into something world class, happily working as an operator whilst also managing and guiding a wider team alongside. I’m as comfortable writing bash scripts for Mac provisioning as I am terraforming an Okta instance or building ETL pipelines for a SIEM. Or coaching others through these same processes.

💪 What I’ve done

🤟 Built Internal Technology many times over

Founding member of the TechOps teams at both Remote and Monzo. Both grew to be world-class teams, admired inside and outside of the respective companies. At Pleo, helped transform the existing IT team into a highly performing TechOps function and spearheaded the development of the Internal Technology group from proposal to implementation.

🔐 Centralised staff data, authorisation and authentication

I've used a varied set of identity tools to radically rebuild and refine the identity and people data systems from nascent or non-existent into end-to-end automated systems seamlessly allowing users to be their most productive based on their assigned role with core technologies like SSO and SCIM along with infrastructure as code, custom API integrations and device trust.

🎉 Made tech onboarding delightful

Multiple times I have built or rebuilt both MacOS and Windows provisioning processes into automated, delightful and quick experiences that leave the user productive and content from minute one. I’ve also done the same on the end-to-end user account lifecycle, creating a seamless experience where from minute one every user is enabled and unblocked.

🚛 Integrated hardware as a service

Worked with vendors, logistics services and their respective APIs. Built a hardware fulfilment network that worked worldwide and encompassed asset tracking, logistics and financial transactions to the point of selling and competing this product on the open market. Lead a team that onboarded and delivered laptops to >1000 people in >50 countries in <12 months.

🏡 Built out offices, hybrid and fully remote teams

Lead on the technical sides of office fitouts from 40,000 to 120,000 square foot and up to £10M, including routed-access networking, internet provisioning, AV buildout and access control all in-house to industry-leading specs. On the other hand I’ve championed and thrived in fully remote environments with truly world-spanning teams executing at maximum speed in a fully asynchronous environment including a team of 3 stretched from US west coast to the Philippines.

🤝 Handled SaaS deals big and small

Extensive experience and comfort managing multi-million dollar contracts as well as negotiating hard for the best price, realising six-figure savings and topping negotiated rates benchmark data. On a wider basis, building solutions for shadow IT and pulling down extraneous platform use to manageable levels.

🧑‍🤝‍🧑 Founded teams and rebuilt existing ones

At Remote, took on the Head of TechOps role and span out a second team to look at hardware fulfilment, including fulfilling requests from our customers in an entirely new product function. At Pleo I took an existing team and rebuilt the values, principles, direction and company perception whilst building a wider group function and incorporating other teams.

⚡ What I’m good at

🔭 Long term vision and executing on it

I’m ambitious and specific with long term goals. I can create detailed plans and proposals with clear iterative steps to get there, and technical fine detail. I'm experienced at presenting these to leadership and gathering the support to execute on the vision.

🙏 End user focus

I’m super passionate about keeping the users I support productive and happy. It gets me up in the morning and drives me and is the source of an immense amount of pride.

👷 Bootstrapping

I can take a process or idea from nothing to something under my own steam (or with a team) and make it something people genuinely want to use/do whilst having a clear vision for how it could best grow beyond those foundations.

🤓 Learning what I don't know

One of my favourite pastimes is taking a problem I have no context or knowledge on and building an understanding from any/every source until I feel qualified and confident in making informed decisions on it. I love to learn and am most happy when I have the opportunity to do so.

⚖️ Managing disparate priorities

The variety and differing priorities I normally see in my role and working style means I am proficient at working across many different priorities and aggressively prioritising and triaging where required.

👪 Managing others

I’ve managed 2 teams at once as well as single teams and product squads and have managed both ICs and managers. I’ve also worked inside of a large (1000 headcount org) to build consensus, change direction and bring an established team into a new approach and methodology. I'm comfortable taking this role as long as I can lead through example rather than through dictation, I can’t stay happy as an “ivory tower” manager.

🤗 Building a safe, ambitious space

Helped direct reports work from ICs up to team managers and progress their career, confidence and knowledge whilst keeping communications open and frank. I presided over the team with the best eNPS scores of any team at previous roles and pride myself on building an enabling, open space for everyone.

🏗️ What I’m bad at (currently)

🧘‍♂️ Work/life harmony

It’s a cliche but for me it’s accurate. I can work myself too hard and lose my sense of time and perspective. I'm moving forward with hobbies and passions to pull me away from this and working on ensuring I internalise what's really important in my life and how best I manage work sustainably alongside this.

🎓 Taking instruction

I can struggle with authoritative approaches and work best when I have autonomy to reach a goal in a way that is agreed upon not dictated. I try and manage this with candid feedback through pre-agreed channels with people where I feel the dynamic building but it’s something I struggle with on a core level. This struggle becomes a lot tougher if I feel the person instructing me has not considered other valid opinions.

🤌 Micromanagement

Just as I don’t enjoy being micromanaged I struggle hugely if asked to manage the absolute specifics of other people’s workload. I am a huge believer in the capability of people if given the support and encouragement to do the best work of their lives without needing someone looking over the nuance of how this happens. For the vast majority of people this works, for a minority they can struggle without very clear structure and guidelines to their work. I’m working on getting better at understanding when this approach is more appropriate and how to best do this to help people with a preference for closer management thrive too.

💕 Sharing the load

My commitment and work ethic means sometimes I can take on more than my fair share of work or knowledge which can alienate teammates. I'm actively working on better seeing the opportunities and ambitions of others not just focussing on the goal at hand. Moving to a more managerial role in my previous roles has helped me address this massively and realise the power and opportunity of delegation.

🗳️ Compartmentalised working

So far I've generally had the privilege of working in environments which are hugely transparent and open and this is something I weave into the fabric of the way I work. As a result I’ve struggled more with working in cultures where communication and feedback are more closed-off and result in a lot of juggling communication channels.