Tough Tech Hiring Guide

Contributing authors: Amy Knapp, former SVP People, Catalant, Susanne Talbot, SLT Talent Acquisition Recruiting, Drea Garvey, Head of HR, Hometap, Sarah Hodges, Pillar VC

As Jim Collins, Author of Good to Great says, “Great vision without great people is irrelevant.”  Getting “the who” right is just as important as “the what.” But how, then, do you consistently find diverse top talent to help you grow your company? How do you get the best of the best to accept your offer and onboard them smoothly to efficiently have them start crushing goals alongside you? Our hiring guide is here to help founders navigate this critical process.

First off: we know you needed someone in that key role two weeks ago yesterday, but our first tip is: wait for the right person. Getting the wrong person is so much more work for you. Promise.

Sketch out a hiring strategy

Before you start posting openings, you might want to think about:

  • Organizational planning: One of the first questions to think about is which skills are critical for this new hire to have - and which skills would be amazing, but aren’t core essentials. Which skills are easy to teach and which ones must be present on day one, for this person to be successful? It’s also really helpful to think organizationally about where this person will fit into the existing team. Who will this person report to and interact with? The answers to these questions will provide you with a role scope to help you create a project plan for filling this position.

  • Budget: What is your cost-per-hire budget? How much are you willing to spend? Think not only about your financial costs - but also the cost of team time and the opportunity cost of missing key milestones without the right person in place. It’s important to get good market comps early on to help set expectations. 

  • Timeline: What’s your goal? Expect a 3-month lead time for most hires.

  • Building team buy-in: Have you thought about who needs to be involved in the process - and at what point? Including key stakeholders in the process builds buy-in and increases the likelihood of a smooth start.

  • Tough hires: Do you have a deep network to help you find a very specific skill set? Would a specialized agency help?

  • International hires: Are you accepting international candidates? Do you have a good Visa lawyer?

  • Diversity and inclusion: Is there bias in your process? How are you going to build diversity and inclusion into the DNA of your organization? In addition to culture and gender, think about cognitive tendencies, skills, and personalities, too. If you don’t have a diverse team yet, perhaps you’d like to bring in extended members of your team - like an SAB member or advisor - to join your process.

Strategic planning: aligning your needs and process

One of the key steps that most startups plow past is around strategy. Although it slows you down a bit upfront, designing a new hire rubric will increase your likelihood of a successful hire. In the rubric, you’ll create a grid of the “need to have” and the “nice to have” skills. Then, you’ll map assessment approaches to these skills - i.e. if you’re hiring a software engineer, perhaps you want to provide candidates with an assignment that will show you what they can do.

Job descriptions: choose your words wisely

Writing a job description is equally important internally and externally. Internally, a job description is a chance for everyone to align on how the role will fit into organizational goals and engagement. Externally, how you word or phrase what you’re seeking may greatly impact who is attracted to the opportunity. Here’s a job description template to help you get started.

Market Data

Make sure that you’re using a good source of data (i.e., don’t use salary.com). If there isn't data for your geographic location, make sure to find a comparable city to estimate. For example: Boston-based companies should reduce salaries by 10% when compared to CA-based positions.

Here are some comp tools to help you out:

How to promote diversity in your search

There are a lot of ways that we unconsciously and consciously bias the hiring process and end up with a homogenous team. Once you have enough people who are very similar on the team, it’s much harder to attract diversity. Diversity needs to be something even formation-stage founders need to be thinking about from day one.

How you write a job description, where you promote the opportunity, how you screen candidates, and who conducts the interviews - all of these aspects of the process can have a big impact on how you build a diverse team.

If you haven’t read Bias Interrupted, you should check it out. The idea is that you can’t necessarily retrain our brains to avoid bias, but you can be aware of bias and set up tactical solutions to create more equitable and diverse organizations.  Joan Williams, the author, has created a ton of free resources to help you and your team tactically plan to interrupt bias in the hiring process, like this guide.

There are also great tools out there to check for gender bias in your job description before you post - like Textio or Gender Decoder.

Sourcing Talent: where to find top candidates

One of the most critical steps in hiring is finding stellar candidates. There are several ways to source applicants and it’s important to take a holistic approach to finding great people for your team.

Networking: leverage people you know

  • Think about creating an employer referral bonus to incentivize your team to open up their contacts. $2.5K - $5K is a typical amount to reward employees.

  • Leverage social media to make sure your whole network knows you are hiring

  • Ask your advisors and board to help you recruit.

  • Start to build your network by getting engaged with the community. Even if it’s not feasible to provide financial sponsorship, you can be present as mentors, volunteers, and resources for diversity-focused organizations and events, such as:

  • Lesbians Who Tech

  • CODE2040

  • All Star Code

  • Hack the Hood

  • Black Girls Code

  • Girls Who Code

  • Yes We Code

  • Girls in Tech

  • CEOX women CEOs

Places to post jobs positions:

Advanced sourcing tools:

There are some more robust sourcing tools like Gem, HireEZ, Teamable, and Fetcher that crawl across a wide range of sourcing sites for you. However, you need dedicated people on your team to manage them. Although these tools can be pricey, many of the tools have flexible pricing for early-stage companies.

Getting help from a recruiter:

The best way to find a great match for your company is to ask people you trust for recommendations. Ask fellow founders and any heads of HR you know - they’ll have great tips for you on people they’ve used and trust. When considering if you should explore working with a recruiter, think about your network first. Do you have strong ties to that particular segment of the community? If you don’t, a recruiter who works with a specific phenotype (i.e., machine learning experts), could be a great way to fast-track finding a great match. Another consideration is time and money. Your time is extremely valuable. How much time can you afford to spend on this hire? What other competing milestones and deadlines are you facing? A recruiter may be a great solution if you are stretched thin.

  • Agencies are helpful if you are seeking a specialized position and don’t have the network to recruit for that position. Expect to pay $25K - $50K for agency support.

  • Consultants and contract recruiters are a great option when you don’t quite have a consistent number of positions open and need help here and there. They can also be used for strategic support and advising along the way. You can expect to pay $75-100/hour for their help with your search.

  • In-house on your team - Typically companies who are post series A and are consistently hiring are going to want to start thinking about building your in-house team for hiring.

Here are some recruiters with whom our clients have had success:

Applicant tracking systems + databases

It’s important not to lose candidates and to track your data to improve your recruiting process over time. You can hack together a Typeform and Airtable if someone on your team has the skills to create a seamless workflow. Otherwise, you can use one of these tools:

Interviewing + Assessing Talent

There are several approaches to designing your interviewing and assessment process; it’s important to review your original skills rubric so you keep the key skills and success metrics front and center.  First Round has a great guide here to explore some skills and questions you may want to consider while interviewing.

  • Behavioral interviewing is when you use past experiences to predict future success (e.g., give me an example of a time when you fit with company culture...)

  • Scenario-based interviewing is when you ask a candidate to show their thinking about how they’d solve a relevant problem they’d likely encounter in the role (e.g., how do you think you’d collect customer feedback on this product...)

  • Assignments can be given to candidates before or after the interview as a way of seeing the type of work they produce (e.g., show us how you would solve this specific technical problem...)

  • It’s important to learn about illegal interview questions so you know how to be professional during the process.

Reference check to hit the ground running

When you’re starting to get serious about a candidate, it’s important to ask for references. Although references can sometimes alert you to red flags, more often they are helpful for getting a jump start on managing your new hire. What are this person’s strengths? What are areas for growth? What can I do, as their new manager, to bring out the best? Here are some standard reference questions to ask.

Making the offer

Once you’re ready, it’s standard to verbally offer the position to your top candidate and then follow up with a written offer letter or an offer letter slide deck. You may want to check out this great Medium post about offers; it inspired the way that Pillar VC makes offers. Candidates will want to know their salary as well as their overall benefits, so you will want to have an employee offer summary ready to go.

Rejecting candidates

Once the offer has been accepted, it’s generally considered good practice to communicate with other candidates to thank them and give them closure. Think about how you want to keep strong applicants engaged for future opportunities, even if there was a better match for this specific position.

Onboarding new hires

Congratulations on landing that great new hire! You led a great process and you can’t wait to have this new person integrated and sprinting alongside you. Before you dive into day 1, it’s important to create an onboarding process that includes:

  • Setting up a great first day - how will you introduce this new person to the rest of the team and the community? What kind of a welcome would feel best for this new hire - a welcome coffee, an all-staff email, or a quiet entrance? Would a welcome present (like some swag) feel super special or a small budget to buy new office supplies? Small gestures go a long way - what do you need and want to have a smooth transition?

  • Conceptual onboarding - setting new hires up for success with the big picture - where are we going, where have we been, how do we do our work and plan to achieve our goals.

  • Tactical and operational onboarding what tips and tools does this person need in order to do their job and focus on the right stuff? What programs does this person need access to? Think about passwords and documents as much as you think about introductions to people.

  • Set up checkpoints and a 90-day review - It’s a good practice to have a 30-, 60-, and 90-day review for new hires. This allows for course corrections and feedback before “business as usual” kicks in. 90 days is enough time to also realize if the hire is not working out as well as you’d hoped - and the opportunity for that conversation has been built in from the start so there are no surprises.

Finally, after the first 90 days are over, it’s time to think about what ongoing management, support, and professional development is going to look like. While those first three months are critical for success - hiring is a long game and not a sprint. The cost of losing great people is significant in terms of time, milestones, and budget, so it’s important to have an organizational strategy for keeping top talent happy and learning while working on your team. A favorite management question to ask regularly: What’s getting in your way and how can I support you?