top of page
  • Writer's pictureArtemis Canada

Dear Artemis: We're a bootstrapped startup. Can you give us hiring tips 'n tricks?

Welcome back to Dear Artemis: Where you ask us tough questions and we use our collective 45+ years of knowledge in the recruiting space to answer them.

Dear Artemis,

We’re a bootstrapped startup. Our VC-backed peers get advice on hiring from their investors. We have non-VC advisors but sometimes we still feel in the dark when it comes to hiring. What advice can you share with us - what should we consider when hiring leaders?

- Founder, Bootstrapped startup

Dear Founder,

Great question! We work with many boot-strapped startups. The advice we’ll share with you is no different than the advice we share with early-stage VC-backed companies, but we know that VCs are often hands-on in providing this advice.

For starters, revisit your strategic plan and look closely at your KPIs + objectives for the year. Determine which leaders/functions of your business are most critical to achieving those objectives, and start there. Ie if you’re pre-product/market fit, consider what addition to the leadership team will get you there the fastest (perhaps a product or hands-on GTM leader is important). If you need to increase retention or your customer lifetime value, that’s a customer success leader. If you’re all aboard the revenue train, you’re looking for a sales leader and so on.

Once you’ve decided which role is a priority, here are some things to consider:

  1. What skills are you looking to assess? If you’re not sure, do you have any mentors/advisors who you can ask? If not, ask us! We’re an email away - - we’re happy to share our insights and what we see as top assessment criteria in the market.

  2. What can you flex on? In other words, what are your must-haves in a leader vs nice-to-haves? If you find the PERFECT leader, can you flex on compensation? If you’re really excited about a candidate but they’re engaged in other interview processes, do you have flexibility on the interview timeline or start date? The more you determine upfront, the easier it is mid-process. A note on compensation - a lot of VCs provide their portfolio companies with some very helpful data when it comes to salaries & equity ranges. Check out our salary snapshots for some more insight into what we’ve seen in the market and we’d be happy to expand on any of these further.

  3. How senior will this leader need to be? When our clients are unsure at the beginning of the search, we “keep the funnel open” and share candidates in two camps: (1) stretch candidates, and (2) the “been there done that” candidates. Our advice is usually to opt for the leader where the shoe fits now and has the potential for growth, vs a leader you’ll need in 2 years (you don’t want blisters!). For example: If you’re at $1M in revenue and are looking for a sales leader, we’d recommend looking for someone who’s done the $0-5M revenue growth, not one who’s done $10-20M. Yes - you eventually want to get to $20M and beyond - but not only is that senior leader going to cost you more, but they might not be as scrappy as the $0-5M builder.

  4. What will this leader focus on NOW and in the future? Be as clear as you can on what this leader will do in the first 3, 6, 9 and 12 months - as well as your long-term hopes. Make sure you find a leader who’s excited about your “here and now” plan, not just the 5-year growth plan. You know better than anyone: For someone to enjoy the startup ride, they need to enjoy the journey as much as the destination (if not more!).

  5. What will your interview process look like? Interview processes with early-stage startups are often fluid as the founder(s) figure it out in real-time - and candidates are understanding of this. But the more you determine upfront, the better. For example, will you use case studies? (We vote no, unless done in a very thoughtful way!) How many steps will the interview process be? Will they meet the other members of your team, and if so, will it be a ‘meet n greet’ or a formal interview whereby the other members have sway on the final decision? Remember: The more cooks in the kitchen, the longer it takes to cook the meal… and it doesn’t always turn out as great as you’d hope.

  6. Speaking of which, will you invite those advisors/mentors into the interview process? Some of our early-stage clients invite their mentors/advisors into the 2nd or 3rd step of the interview process, once the candidate has met the hiring manager and is excited about the opportunity.

  7. What geography are you open to hiring in? Keep in mind, different provinces and states have different employment laws. Talk to your lawyers if you’re opening up a job Canada-wide. For example, an offer letter to a Quebec-based employee will look vastly different than an Ontario-based employee. We also wrote a blog to help a US company looking to hire in Canada.

  8. Will you hire solo, or work with a search firm? Here are our thoughts when another leader asked us this on Dear Artemis.

And, in no particular order, here are some other Dear Artemis answers that might help you:

We hope this helps. As always, we’re here to answer any questions you have. If you’re a bootstrapped (or VC-backed!) startup with questions on your next hire, email me at I’m happy to offer a pro bono advice session catered to you and your situation.

Happy holidays - we hope you get to unwind and relax over the break.

See you in the new year!

- Negin & the Artemis team


bottom of page