As a tech startup founder you have many jobs. One of the most important ones early on is hiring.

By its very definition, a startup is “a new business developing a unique product or service to scale rapidly, often under conditions of extreme uncertainty, with the goal of becoming a large, valuable company rather than a traditional small business.”

Which means your goal as CEO is to assemble an insane team that can move mountains and do what’s never been done as quickly as possible. To succeed you need the best talent; you must have a talent advantage. For a tech startup in particular, it means hiring great tech talent.

This is an obvious contradiction for a new business, because the best talent generally wants (deserves) to be highly compensated, and early-stage startups don’t generally have much money (yet). So as CEO it is your job to find, vet, motivate, onboard, and nurture this talent in a way that allows you to move those mountains.

We are actively hiring technical talent for our startup, and I am learning a lot about what it takes to build a great team. Here is how I think about hiring tech talent:

When To Hire

First, don’t hire until you can’t avoid it. It’s important that your founding team thoroughly understands and experiences the processes that you will at some point delegate to future hires.

Again your funds are limited, and you are inventing the future. So you can’t afford to spend money hiring people that your business isn’t prepared to put into a successful position. When you first start out as a founding team you are forging the path.

And no matter how big the chip on their shoulder, how motivated, how excited - an employee will never feel as deeply connected to the success of the business as its founders. It’s like the difference between a dad and an uncle.

The founders must experience what they delegate first so they can lay the groundwork. You must prove there is a path, and once you can see that path you can begin to bring others on to help you traverse that path more quickly.

Before you’re ready to bring on tech talent, I’d argue that you should have the following:

• A product in the market already (an MVP) with paying customers

• A 3-6 month product roadmap in place

• An established systems for managing projects

• You should generally feel a bit capacity-constrained

For each startup this might look a bit different based on industry, funding strategy, etc., but the general principles are the same. For most businesses this will be after you’ve been up and running for 6-9 months, sometimes earlier or later.

Now I’m not saying you can’t be on the lookout for potential future hires before you reach this place (always be recruiting), but you shouldn’t start a hiring process until you’ve gotten here.

The Hiring Process

Then, once your business has checked the qualifying boxes above and you’re ready to start actively hiring, the general process will look something like this:

1. Outline the Role and Expectations

2. Post the Job to field candidates

3. Phone Screen any qualifying candidates (20-30min)

4. Technical Interview the top 4-8 candidates (90min)

5. Do a Final Get-To-Know meeting with your top 1-2 candidates

6. Offer & Onboard: and get paperwork signed, get started!

1. Outline the Role 

First, write out a one-page job description. This should cover the important aspects of your company, the role they’ll be filling (structure and expectations), and their desired qualifications. It should also motivate why someone would want to work at your company in the first place (the best candidates will need you to sell them the role). I write a job description like this:

• Who Are We: what is your company building, how does it work

• Why Work Here: pitch why your startup is exciting and worth working for vs. other higher-paying jobs (growth trajectory, ground-floor experience, etc)

• The Role: what they’ll be doing, what are potential projects, why is it awesome

• Qualifications: what background/skills are critically important for success

• Structure: what is the timeline, pay structure, expectations

For an early-stage technical role (or any role in general) I’m a strong advocate for a contract-to-hire structure, ie. they join in a timebound project-based role, after which you assess if it’s a good fit before offering a full-time employee position. It’s a bit like 90-day Fiance; both parties deserve to feel out the relationship before you commit to something longer-term with big investment and upside.

2. Post the Job

Once you’ve outline the job, you need to get it in front of as many qualified candidates as possible. There are many ways to do this, my advice is to leverage your network if you have one - avoid job boards that can be easily scammed or expensive recruiting firms.

For me we just post on LinkedIn, directly to the feed, that we are hiring with role details and ask qualified candidates to send us a DM. This maximizes reach while filtering for candidates that are already somewhat connected to you and puts the action on them to reach out.

Doing it this way on our latest posting we received ~60 applicants via DM’s. From there ask them to email their resume (this is an intentional double screen from spammers). Save all of these into a Notion table so you can keep track of it all.

3. Phone Screener

Once you’ve gotten people to apply you then need to assess their fit for their role. Your goal with the posting should be to get a good pool of candidates >25.

Go through their resumes and LinkedIn profiles and pre-screen anyone who doesn’t match your minimum qualifications. In my experience this will filter out between 25-50% of applicants out the gate (don’t waste anyone’s time interviewing unqualified candidates). Once you have your qualified candidates on paper you should conduct an initial phone screen.

A phone screen is a short, 20-30min interview via phone or video chat with the goal of identifying your top 5-10 candidates worth moving forward with. Typically you will have time for 4-5 questions high-level quesitons (save more in-depth technical questions for a technical interview, next step). I structure a phone screen like this:

1. Quick Intro (3min): set context about the company and interview

2. Your Questions (15min total): ask questions to gauge their experience and proficiency in your core areas (ex: Python, pipeline orchestration tools) in their own words. You should have a rubric for assessing how they answer these questions, see below

3.  Their Questions (5-15min): Save time at the end to answer any questions they have about the role. This will typically be things like expectations, roadmap, etc; if they show up without any questions its a red flag.

4. Technical Interview

After you’ve completed phone screens, go through each candidate and score their answers according to your rubric for each. Ideally you can transcribe/record the interview so you can easily go back through and assign points for how they answered.

From the phone screens your goal is to narrow in on a set of 4-8 candidates worth doing a more in-depth technical interview with. The technical interview will look like this:

• Duration: 60-90 minutes in length, answer 4-5 coding questions

• Format: They share their screen in their coding environment and work through the quesitons 1 by 1, talking through how they are solving the problem

• Tools: You may choose to allow them to use Google Search or AI if you like, just make sure it’s clear that you expect them to show you all of what they are doing and not cheat. ¹

• Goals: Again you should have a rubric to gauge success for each question. Getting right answers isn’t necessarily the objective, it’s assessing how they solve problems and whether or not they can actually do what they say on their resume.

Within a technical interview you might choose to do a few standard coding problems to understand things like basic Python skills or ability to understand and manipulate your data schema, you may also choose to do scenario-based project management quesitons (ex: 'how would you handle a situation like this…’) Here is an example question:

5. Final Get-To-Know

Once you’ve gone through your top candidates with a technical interview, again you should assess performance based on the rubric you’ve outlined for each question. You might include scores for right/wrong answers, how they approached solving problems, or whether they addressed important aspects of each skill you are assessing.

After you’ve done this you should have a sense of your top 2-3 candidates, both in terms of their performance and in the touchy-feely way you get from spending 90min watching someone solve problems.

With this, before making any offer, I like to do one final phone call (or in person lunch if possible) just to talk through any final considerations (ex: career goals, availability in the coming 60-90 days, any schedule conflicts or visa considerations). Generally no agenda other than to let them ask any remaining questions or go over any key sticking points. This is helpful for two reasons:

1. After you’ve thoroughly assessed someone’s technical skills (which should be the case after the 1st two interviews) the ‘tiebreaker’ is often how much you like spending time with them as a person. Ideally on an early team it should be someone you genuinely enjoy spending time with

2. For a contract-to-hire role in particular, the 60-90d contract period often means they will still have another job (likely their old day job). You want to broach this topic sincerely and gauge the dynamic so that you understand how the transition will work when/if they come on full-time.

You’d also be surprised the % of prospects who turn down an offer letter. It may be safe to assume you will not land your 1 or 2 choices, for the same reason I discussed at the beginning of this blog (the best talent is competitive, it’s a 2 way street!). Having one final get-to-know call with your top few candidates mitigates this risk.

6. Make the Offer & Onboard!

Finally, once you have found your person - make them an offer! The offer letter should generally be about 1 page in length and cover the following key info:

• Title + brief job description

• Start date (and end/evaluation date if contract-to-hire)

• Compensation (hourly rate)

• Reporting structure

• Working location

• Any hiring contingencies (ex: background check)

If they sign then you are free to begin the onboarding process! This usually involves some additional paperwork (I9, W4, NDA, Direct Deposit Info, etc.) which you can now handle mostly with payroll software tools like Gusto.

Anyways, I think I’ll stop there and save more for ‘onboarding’ later. For now hopefully that’s helpful on your tech talent hiring journey. Will probably add to this later.

Bye for now,
Ramsey

1  We’ve seen many examples of candidates trying to cheat with AI tools like Cluely during technical interviews… not great but becoming more common. More on this here.