9 Tips for Scaling Your Engineering Team After Your First Big Funding Round

This is a guest post from Olly Headey, a tech entrepreneur based in Edinburgh. Olly co-founded FreeAgent — the cloud accounting product of choice for savvy freelancers — and helped scale the business to over 120,000 customers and 260 staff.

Raising a large Seed or Series A round is a huge milestone. It demonstrates you’ve built a product that investors believe has huge potential, and they have faith that you can scale the business. For tech companies, the first priority is often scaling the engineering team. I grew FreeAgent’s engineering organisation from 1 (👋) to over 100 people over the years. I made mistakes but I learned a lot, so here are 9 tips to help you avoid a few common pitfalls.

Let’s get into it!

1. Build your network

There’s an old saying, “it’s not what you know, it’s who you know”. The point is a good one: relationships matter. Connections matter. Talking to people who have been on the same journey about their experience can be enlightening and very helpful. They can offer advice, recommend potential hires, invite you to networks and connect you to others. People are usually very willing to spare time to talk about their journey, so don’t be afraid to ask. Use LinkedIn, talk to your investors, look for Slack groups or discussion lists for founders and CTOs.

2. Have an idea of what the end structure of your engineering team is going to look like from the outset.

Will you split via features? Product vs platform? Back end vs front end? Different product lines? You should be aware of Conway’s Law and read Team Topologies to educate yourself about organisational design. This vision is great for your own peace of mind, and it will allow you to articulate it to interviewees. They will ask. It’s no problem to change it later as things evolve, nothing is ever set in stone.

3. Have a clear idea of what each engineer is being hired to do.

You will understand your near-term roadmap and know the features you want each person to ship, whether they are full-stack generalists or front-end specialists. Being clear on this will allow you to better sell each individual opportunity and help you close hires. It will help you stand out. The best engineers will have their pick of the crop, so your opportunity needs to dazzle.

4. Hire someone in a talent acquisition role ASAP.

This will save you time, you will learn lots from them, and you’ll probably end up with a more efficient and diverse pipeline because of it. They will help you craft and optimise your job ads. They will polish your Glassdoor and LinkedIn company profiles, and they will be experienced in recruiter and candidate negotiations — you don’t need to spend your time doing that. Just make sure you forge a close relationship and learn how they operate. It’s gold dust. And be sure to use an applicant tracking system (ATS) like Workable — it will be a big time saver.

5. Spend an inordinate amount of your time on hiring.

The return on investment here is huge. It will mean running interviews (you should interview every candidate personally), experimenting with acquisition channels (recruitment firms, LinkedIn, Cord), and funnel/pipeline optimisation. Gather all this data (your ATS will help) and analyse it to make sure your time to hire is as fast as possible — strong candidates will have several opportunities on the go, so first to offer has the upper hand. Ask for feedback from every candidate (hired or not) on their experience and how it can be improved. Now is the time to invest in developing your employer brand, so think about how you’ll increase awareness using LinkedIn, Twitter, speaking opportunities, even an engineering blog.

6. Only hire people who meet your (presumably high) quality bar.

If you’re not hiring fast enough, don’t lower the bar. Increase your hiring budget, start a candidate referral scheme, broaden your reach (different recruiters, more adverts, run hiring events) and improve the overall package you’re offering as much as you can (base salary, equity, bonus, pension, health insurance).

7. Have fixed start dates for new hires.

Only have new people start every two weeks with no exceptions. This frees up everyone’s time (only one induction every two weeks!) and will keep your energy levels high. It’s also nice for new hires to arrive with others on their first day. It’s good for culture.

8. Ensure you have a clear onboarding plan for each new hire:

Week one, month one, quarter one. Buddy them up with an existing engineer so they can get up to speed quickly with tools/processes (ship something in week one!), ask questions and absorb the working culture. Set them up with 1–1s with key people across the business — not just your engineering team. Ask new hires to document how things work if this hasn’t been done in a team wiki (you’re using Notion, right?) so it’s easier for the next person.

9. Introduce a management layer sooner rather than later.

You can probably manage 10–15 people directly at a stretch, but it’s better for everyone if you don’t. Are there existing engineers who have experience of management and want to take it on? Consider doing this despite the short term hit it might have on velocity because your earliest managers, while you’re still a smallish team, will still be able to contribute at some level. Have those conversations early. Either way, ensure you hire a couple of engineering managers who have worked in startups before, used to be hands-on and are aligned with your values.

Bonus entry!

You can ignore this for a while but it could save you time in the long run if you’re scaling fast. Standardise IT equipment. If you’re in the Mac world, pick something like 14" M1 Pro, 32GB RAM, 1TB disk) and don’t deviate. Use Fleetsmith (or maybe Apple Business Essentials) so you can have laptops ready to go out of the box. Consider keeping a small supply ready to go so it’s not a blocker — current lead times can be problematic. If people are fully distributed, give them a stipend (£500–1000) to buy accessories and make this repayable if they leave within 12 months. If you’re in an office, standardise monitors and buy in bulk. Track this capital asset inventory — dates, costs, serial numbers etc (a spreadsheet is fine). You’ll be thankful later.

All this work means your engineering velocity can take a short-term hit but it’s a necessary investment. You as CTO can do the lion’s share and insulate your engineers from unnecessary admin burdens so they can keep focused on delivery. Until we had over 30 engineers, I would review and filter all CVs, undertake initial phone screens, arrange interviews and get candidates through the test (yes, I made the mistake of hiring talent acquisition too late! 🤦‍♀️). Engineers would only get involved at the code review and final interview stages when we’d filtered a high percentage of the candidates, but — crucially — still early enough to ensure they felt intimately involved in who joins the team.

The processes you set up early in the life of your company can be remarkably resilient and stay around for years, even decades. Including the bad ones. This is why it’s so important to invest in getting it right from the start: if you don’t build on solid foundations you’ll end up with a house of cards.

Best of luck! I’d love to know if you found this article useful, and feel free to reach out if you think I — or the broader Point Nine team — can help you on your scaling journey 🚀✌️