How To Bootstrap Your Startup’s HR (And When Not To)

Tips, Tricks, and Tough Lessons Learned. 👇

As a founder, you’re naturally scrappy. You’ve probably done everything (from the financials to the hiring and product decisions) yourself. But lately, something feels different. Maybe you’re months behind on hiring the key people that you need, or your current team members are asking for career plans.You know you want to be a great place to work, but you don’t think you’re big enough to hire HR. What next? In this guide, I’ll walk you through some of my favourite tools and tricks to build a solid HR foundation on your own — no hire required. I’ll also tell you exactly when it’s time to give up the solo act and bring in a professional.

PS: Note that this guide focuses on Canadian startups, but should be generally applicable anywhere.

PPS: Keep reading for a special announcement!

Problem: You’re in administration overload

Maybe you’re running payroll yourself, or, as more than one CEO has confessed to me, keeping all your contracts in a box. You’re furiously googling safety policies and laws on paying out vacation. Or, maybe you’re not doing any of this at all, and are praying nothing bad will happen (because it hasn’t yet, right?). You don’t run the rest of your business based on chance, so why put your head in the sand?

Get started:

  • Let’s get you out of the banker box of shame- you need HR software. A good system stores and reports on employee information, helps with benefits and payroll, keeps contracts handy, and even tracks vacations. Two great options are the Toronto-founded and easy to use Collage, and the slightly more feature-heavy BambooHR. If you’re over 10 people, this software is essential.
  • You need policies on things like health and safety, and standardized employment contracts. Open source policies are a thing if you know where to look and have the time to adapt and customize them.

When to get HR:

HR software is generally easy to set up, but it does require you to have an idea of the guidelines you want it to handle. It also requires you to keep its information current and relevant. When the record upkeep becomes too time consuming and when you want customized programs and policies, hire a pro. If you’re getting tapped on the shoulder too often with questions about benefits, it’s time.

Problem: Recruiting isn’t going fast enough.

You’ve secured funding and defined your product roadmap. You figure you’ll hire a few developers, maybe a designer and product manager. You post some jobs on your website, but somehow the applications aren’t rolling in. Your managers are too busy doing manager stuff, and the process with the candidates you do have takes forever.

Get started:

  • Get in sales mode. What’s different and unique about working for your company? Wealthsimple, an innovator in the fintech space, offers benefits suited to financial wellness. FreshBooks highlights its quirky culture by publishing its annual halloween festivities. This isn’t a list of daily tasks we’re writing- it’s a piece of marketing! Once you have a draft, Textio is a tool I love. It uses machine learning to help you craft the best posting possible.
  • Posting your newly-amazing job on your careers page won’t be enough. Be sure you’re on specialized sites such as StartupNorth, TechVibes, AngelList, and Stack Overflow.
  • Host meetups and events in your own space (it makes you memorable to attendees) and send your best people to speak at other events. People want to work with other smart people who can teach them new things.
  • Now that you’ve got them, how to manage all those candidates? Greenhouse and Lever are at the top of the game when it comes to organizing your recruiting. They’ll also give you an idea of key metrics like which sources are bringing you the best hires, and how long it’s taking each team to interview.
  • Repeat after me: no hiring over coffee or beers! We all think we’re much better judges of character than we are. To make a real weighed decision, you need a more scientific process. Not sure how to design a great interview? This Re:Work guide from Google is an amazing resource.
  • Found the right person, but not sure what to pay? Aside from chats with your fellow founders, PayScale, Glassdoor and LinkedIn have salary tools that are useful.

When to get HR:

If you still aren’t getting the right candidates, or if your managers are too busy to do all of this effectively, level up. Recruiting is a lot of work, and you’ll need to move quickly. A pro can also help you develop a better interview process, a full compensation strategy, and help you craft the hiring plan you’ll need to achieve your product goals.

Problem: You’re no longer flat.

In the early days, it’s likely that no one thought about reporting structures. You were proud of being flat. It posed no problem- issues could be worked out easily with a chat across the table. Suddenly, you’re hearing that people want growth plans and career paths . Your leadership team is overwhelmed and can no longer manage 10+ people each while executing and playing visionary. The right thing to do is to get more people into management, but your top performers have no experience with that. How can you help them?

Get started:

Don’t be afraid to ditch the flat structure. Well-trained, empathetic managers are key to driving performance. If you’re in Toronto, UpSpark’s tech lead training is a great place to send newly promoted engineering managers. For startup focused manager training in all disciplines, Melissa and Johnathan of Raw Signal are the go-to’s. In the meantime, Google’s re:Work guides on management and countless books are there for inspiration. How about a manager book club?

When to get HR:

When those managers need an ongoing partner and guidance. When people are asking for defined career paths and formal feedback, like reviews. In my experience, this is all likely to happen around a headcount of 50, or shortly after leaving the “flat” zone.

Problem: You’re scared of being the next Uber.

You’ve read about the scandals, and they terrify you. You don’t have a harassment policy, but you don’t think it will happen at your company. You want to be inclusive, but aren’t sure how to get more diverse candidates to apply.

Get started:

My advice is to make sure you have an inclusive culture first, before diving into recruiting. In fact, I wrote a whole post on it. Here’s more on how:

  • Open source some policies on harassment and on parental leave. Great resources include the TWG/Tech Girls Canada collaboration “Change Together”, and the newly launched Parental Leave Playbook.
  • Facebook has also open sourced some great unconscious bias training videos. You can watch these with your whole team and discuss them afterwards.
  • Be sure to have an anonymous feedback process that goes straight to you- even a google form will do.
  • If you have employees that are also interested in making an impact here, consider forming a task force. One idea I really love is building an apprenticeship program to develop a pipeline of engineers from less traditional backgrounds. Rangle.io’s Bridge program is a great example, run and managed by employee members of their diversity guild.

When to get HR:

This is a tricky area, and one where I really recommend at least having an occasional onsite professional (like a part time contractor) on hand. Some people will never be comfortable talking to you or their manager about tough issues. If you do have absolutely any harassment complaint arise, seek help immediately. Ideally, have a professional assess and strategize your policies, processes, and benefits before anything goes wrong.

Problem: You don’t know what people think at all.

You used to have the pulse on everything- now you’re not so sure. Maybe because you’re so busy or because you’re “the boss”, you feel like people come to you less and less. It’s lonely at the top, and you’re worried about missing key information.

Get started:

  • Keep it personal. You can’t meet with every team member every week, but you can hold the occasional skip level.
  • Collect some data! CultureAmp is my favourite tool for surveys. I use it for everything from measuring happiness to seeing how a training program affected performance. I’m nerdy about people data, and I find it’s the best at catching trends. Other options are TinyPulse, which gives you less but more frequent data, and Toronto-based Fortay.

When to get HR:

The tough thing about asking people how they feel and want they want is that you have to follow up. If it surfaces that everyone wants 360 reviews or a formal mentorship program, you’ll need the time and expertise to carry that out. Otherwise, you’ll risk losing their trust. Why should they give you feedback when nothing’s ever done about it? If it’s more work than you can handle, bring in professional help.

What next?

With so many great tools available, bootstrapping your startup’s HR has never been easier. If you have the time and the will, you can begin to build bedrock on your own. However, for those without the luxury of time, or reaching the next step in their growth, it won’t be enough. Companies need someone experienced that they can trust, and who understands the unique challenges of a startup’s culture.

That’s why, after years of building HR at top startups (like Wealthsimple and FreshBooks), I’m launching Bright + Early.

Bright + Early is a modern HR consultancy that’s laser focused on helping early to midstage startups, part time. We use design thinking and an iterative, inclusivity-focused approach to do work that grows people, teams and companies. No culture compromise required. If you’ve realized you need a little bit of help (or a lot of it), let’s talk about working together. 🚀

Happy building!


*Illustration by Laura Callaghan

Side note: For any readers who are already HR pros, I’m looking for my replacement to lead the People Operations team at Wealthsimple. This is a really exciting opportunity to take a company beyond the stage I describe above: specifically, from a midsize company to a global one. It’s a VP level role working with an absolute rocketship of a team. If you’re experienced with and passionate about taking companies from 200 to infinity, contact me directly.