How I Scaled a Company from 7-35 in a Year

For companies under 30 employees.

Hi! My name is Sam and I use they/them pronouns. I was previously an early employee at 2 YCombinator startups, and managed to scale another from 7-35 in a year. I’ve handled almost the entire sourcing and recruiting and interviewing cycle, except for software engineering technicals and negotiation. I plan on updating this document every now and then.

My Twitter: @samchai__

My LinkedIn: https://www.linkedin.com/in/samanthachai/

The North Stars

  • Understand exactly what your company needs
  • Having a fully transparent, explicit, fair process with the candidate
  • Be nice, even if you don’t feel like it.

Understanding The Scope of the Role

As a founder, you’re probably doing a million things at once. Because of this, founders have trouble understanding exactly what they need out of a hire. Rather than thinking about what you want, think about where you have the most time sunk - and how hiring someone would reduce the time sink and increase bottom line revenue by X%. Min/max your hire by understanding where you’re the weakest in time and money.

Recruiting can be a huge time sink, if not done effectively. Run tests often, and optimize everything because it can be incredibly repetitive.

Rigorously interview the department heads that you’re hiring for. Although a startup can have a company-wide culture, departments can have very different cultures. For example, many engineering departments work asynchronously, while sales and marketing can be quite collaborative. Understanding these differences in departments can give the candidate a truer understanding of what their work environment will be like.

Questions to ask departmental heads (or yourself):

  • What’s the full tech stack? (For example, the job posting might say CRM software, you may use Hubspot, and the candidate uses Salesforce.)
  • What is the culture like?
  • What is the management style like?
  • Why do you think that this management style is the most efficient for your team?
  • What are the coworkers on your team like?
  • How is performance measured?
  • What will the 3, 6, 12 month plan be for this candidate?
  • Why have you failed to retain your previous team members?
  • What is the gender/racial makeup of your department?
  • How can the candidate grow in this role in the next year?
  • What’s the largest time sink for you?

Essentially, ask all questions a candidate would ask you. This will enable you to write a better job description and help the department head determine how they can min/max this hire too.

Writing a Job Description, and Optimizing your Job Posting

Compile job descriptions from your direct and indirect competitors, and then frankenstein it to suit your needs. Use content from your interviews with department heads to fill in the gaps. Job board websites also post sample job descriptions, which you can also pull from. When a candidate physically pulls up your job posting on a site like Angellist or LinkedIn; they only see the top half of the job posting. There are two schools of thought on writing about your company, and it’s up to you to choose how you want to optimize your job posting:

  • 1. Write A LOT about the company; your VCs, how much you’ve raised, why your mission is important, etc. Your job posting will show up higher on job boards and helps sourcing, but the candidate may skip over it.
  • 2. Keep it short and sweet. Candidates are usually applying to multiple jobs at once; getting down to the point faster could push them from reading -> applying. On the downside, your job posting may not show up high on job boards.

Additional Items for your Job Description:

  • Whether it’s a contractor/employee position
  • The number of hours you expect the employee to work. Be honest here. If you’re a startup that works 60-80 hours a week, say it. If you hire a candidate who quits after 2-3 months, it’s a long term larger money and time sink.
  • The time zone that you want your team to work in
  • Whether it’s remote/in person/hybrid
  • The salary range. Someone who is passionate about what you’re building will be okay with this. There is no rationale to hiding the salary range if it’s a deal breaker for the candidate - you’ll waste your time doing multiple interviews and then realize it’s not a fit.

Where to Post Your Job Posting

  • LinkedIn; you get one free post which LinkedIn gives to you. If it’s your first time posting a job on LinkedIn, your first post will get a lot of applications, because LinkedIn wants you to convert you to pay for more job postings. If you’re hiring for multiple roles, you may want to prioritize your most important hire on LinkedIn.
  • Indeed; they’ll send you more applicants if you select that you’re hiring more than 1 person. You can make duplicate job postings and A/B test which options to tweak.
  • Angellist; but I’ve personally found that it results in the lowest number of applications compared to Linkedin or Indeed.

Optimizing your Job Posting on Job Boards

  • Select locations that have the highest concentration of that role (for example, Washington and California have the highest concentration of SWEs)
  • Create deal breaker questions when the job board prompts you; e.g. “Do you have at least 1 year of Javascript experience?”. The job board won’t immediately reject the candidate if they answer “no”, it’ll sort them into a different bucket. Let the job board do the hard work for you.

Sourcing Candidates

Sourcing candidates is about optimizing your time to find and speak to the best candidates.

Create a spreadsheet of a poach list from your direct and indirect competitors. I also suggest creating an anti-poach list; when you eventually hand this off to a recruiter, you want to ensure you’re not poaching talent from your friends’ startups. You can also poach from companies that are in the same vertical (medtech, biotech, B2B SAAS), because you’ll find someone with the same cultural values as you. Lastly, you can also poach from product adjacent companies; find people who are building for your customers AND their customers.

You’ll need LinkedIn premium to be able to search for candidates, as LinkedIn limits the amount of searches you can make per week. Search for “(role you’re hiring for) at (companies you want to poach from)”. Screen by relevant job title, and then open each profile in a new tab; so you don’t have to wait one by one for each individual profile to load. It makes a difference when you’re looking through 100s of candidates for hours.

Selecting Candidates to Reach Out To

By now, you should fully understand 1. What your culture is like (or culture on the departmental team) and 2. The hard requirements you need to hit. I reduce the hard requirements to mostly 3-4 keywords, and if a candidate hits 2 of them, I reach out to them. Creating a criteria with your keywords ensures a fair hiring process. Ignore the school and the degree, unless you’re hiring for a highly technical role.

  • Introduce yourself. Tell the candidate why you’re interested in them, and keep it short. Compliment the candidate.
  • E.g. Hi (candidate name), My name is Sam and I’m a recruiter at Hypercare. (Candidate name), your work experience at (two companies they worked at) caught my eye. I’d love to set up a 15min to chat about it! Best, Sam
  • ^ I usually get a 20% response rate with this type of message to candidates. I’m still figuring out how to optimize this, but ⅕ isn’t bad.

At this point, the candidate either provides their availability, or asks further questions about the potential role. If they ask about the role:

  • Send them the link to the job posting
  • Send them to a notion page about the company culture
  • Then ask them “What do you think?”. It’s important to have an actionable or direct question at the end of your messages with candidates so they don’t have to think about how to respond.

Schedule the call, but if the candidate declines, you can still ask them why.

  • E.g. (Candidate), thank you for your response. I’m not trying to push the job on you, but I was wondering if you’d be willing to provide feedback to me on how I can optimize my pitch?

Usually, candidates will talk about their dealbreaker at this point “you don’t pay enough, the tech stack doesn’t match my current skills, etc.”. Or they’ll actually tell you how to make it better.

  • You may be able to get through this objection, seeing if you can meet their dealbreaker.
  • If not, thank the candidate and let them know that you’re happy to help them in the future with their job search or career. A “no” now doesn’t mean a “no” later. Be nice, because they could be your future employee.

The Screening Call With the Candidate

  1. Explain what the company does in simple terms. Don’t use buzz words, just be as simple as possible to avoid confusion.
  2. At this point in time, DO NOT explain what you’re looking for. Dodge the question. During this time on the call, you’re courting the candidate and selling them the vision of the company. On top of that, you asked the candidate to explain what THEY do in your initial LinkedIn message. Otherwise, they may change their pitch to fit the role.
  3. Ask the candidate about their experiences. Let them explain, and ask insightful questions. Be naturally curious.
  4. Pitch the role to them based on their experience.
  5. If it works out, tell the candidate what the interview process is like.
  6. The timeline that you want to hire for
  7. How many steps/interviews there are, the content of the interviews (technical, non technical interviews, coding challenges, culture interviews, etc)
  8. When you’ll be able to send them the invitation to the next stage interview.
  9. Tell the candidate you can adjust this hiring timeline based on their other offers.
  10. Lastly, let the candidate know that you’re busy, and you may make mistakes. Tell them that they’re welcome to follow up with you whenever.

The Email After the Screening Call

  1. Thank the candidate for doing the screening call with you.
  2. Explain the interview process again, with the amount of minutes that each interview will take, and the timeline that you want to hire/extend an offer in.
  3. Attach a calendly link where the candidate can book the culture call with you. Sidenote: on the calendly page, title your event as “Job Title + Stage of Interview”, attach a link to your notion page on culture, and your phone number in case candidates have technical issues on the call and need to call you instead.
  4. Attach the job posting, and a pdf on your company culture or notion page.
  5. Thank them again, and let them know that they can follow up with you whenever.

The Interviews

I order my interviews as the screening call -> culture interview -> technical interview -> negotiation/logistics. The screening call goes first, so it’s low commitment for both you and the candidate, and you’ll know immediately if it may be a fit. I do the cultural interview first, because it doesn’t matter how technically skilled you are if you’re not kind or don’t share the same vision. For the technical, I wouldn’t suggest anything over 2-3 hours. If you know exactly what you’re looking for - do you really need 10 hours to determine if a candidate is technically qualified? If you absolutely have to do a technical longer than 2-3 hours, compensate the candidate.

Prepare a criteria/marketing sheet that ranks each of the candidates’ skills for the culture and technical interview. We all have internal biases, and this mitigates that and ensures fair process for all candidates. This also makes your decision easier - the more you eliminate candidates at each point in your funnel, the less work you need to do. Give each candidate the exact same culture questions and technical problems, and plan this ahead of time.

The Culture Interview

  1. Pull up the candidates linkedin, and your criteria to write in.
  2. Thank the candidate for joining the call with you.
  3. Start off this call introducing yourself, and explaining what your company does in simple terms.
  4. Explain the agenda of the call
  5. E.g. “We’re going to start off with the company and the role, then we’ll go into your background, and lastly the interview questions”.
  6. I find it counterintuitive to have the candidate start off with themselves - they’re going to ask their deal breaker questions at the end of the interview instead of mentioning it in the beginning.
  7. I explicitly tell the candidate “Any questions you have for the end of the interview, you can ask them now”.
  8. Then explain the role; everything in the job posting such as the roles and responsibilities, the benefits of working at your company, the hours, the salary, etc. Anything that can be a dealbreaker. When candidates are applying to jobs, they’re applying to multiple at one time, quickly. They may not remember the specific details that are the dealbreakers, or see it in the job posting. At this point in time, the candidate will bring up the deal breakers. Ask the candidate if anything that you explained is a dealbreaker. If it is, you can end the call. If it isn't, move on to the next step.
  9. Ask the candidate what their questions are. Answer them thoughtfully, thoroughly, and directly.
  10. Ask the candidate to explain their background.
  11. Ask your interview questions
  12. Thank the candidate for completing the interview.
  13. Let the candidate know that you’ll get back to them by the end of the day. Since you’ve already filled out your criteria, you should know exactly if you should proceed or not.

The Email After the Culture Interview

  1. Thank the candidate for interviewing with you
  2. Provide feedback to the candidate about what they did well on, and what they didnt.
  3. Let them know the specific details about the technical interview and how they can best prepare.
  4. Candidates should not have to guess what you’re expecting - they have the skills, or they can study and brush up. People can’t hide their technical proficiency, so just be upfront.
  5. Attach a calendly link where the candidate can book the technical call with you. Sidenote: on the calendly page, title your event as “Job Title + Stage of Interview”, attach a link to your notion page on culture, and your phone number in case candidates have technical issues on the call and need to call you instead.
  6. Let the candidate know they can follow up on the status of their application at any time, or reach out to you for any questions.
  7. Thank them again.

The Technical Interview - Software Engineering

Unfortunately I don’t know too much about designing a proper software engineering technical interview. If you’re a software engineer and reading this - please DM me @samchai_ and let me know how you run your technical interviews!

The Technical Interview - Sales

At this point, you’ve probably already done a few sales and have a rough idea of what your sales process is. Explain what you’re currently doing, and what problems you’re facing. Look for people who have built sales pipelines relevant to what you’re building, and have them explain to you what you can improve. They should have an answer to the problems you’re facing. Let them explain the relevant tests they’ve done, and why each experiment worked or didn’t work.

Some questions to ask the sales candidate:

  • What is your average deal size?
  • How long is your average sales cycle?
  • What quotas did you need to meet at your previous job? Did you meet them?

The technical interview is a bit tougher, and can go in multiple directions. Let your intuition guide you, and be naturally curious.

Then:

  • Thank the candidate.
  • Let the candidate know that you’ll get back to them by the end of the day. Since you’ve already filled out your criteria, you should know exactly if you should proceed or not.

The Negotiation

I’m good at negotiating my own salary, but don’t have any experience dealing with candidate negotiation. If you’re a founder that’s negotiated before, please DM me @samchai_ and let me know how you negotiate!

The Contract

There’s a lot of templates online, but make sure you cover:

  • An NDA
  • A Non-Compete
  • IP Protection
  • Start and End Date
  • Expectations for the role, again. If you need reason to fire the employee, you can refer to these specific expectations as reasons why you needed to fire them.

Don’t stop your hiring process, even if you’re confident, until the candidate signs the contract. Try to aim for three candidates you want to extend an offer to.

And That’s It!

If you found this helpful, want to provide any feedback, or have any questions, let me know on Twitter @samchai__ or LinkedIn: https://www.linkedin.com/in/samanthachai/! :)

Here are some of my personal thoughts on recruiting:

  • I fail to understand why recruiters are assholes to candidates. I also fail to understand why companies are assholes to candidates. For example, some companies require that the candidates sign a contract within X time. This just leads to the candidate signing, and then ghosting or letting you know that they can’t work for you anymore. The candidate you extend the contract to will be a force multiplier in that area of need - just be nice.
  • I don’t swear while I interview candidates. For minorities and POC, this can be unnecessarily intimidating.
  • It’s important to build a diverse company from the beginning - if you let your biases get to you; they can compound and subsequently limit your talent pool. E.g. a female won’t want to be the only female on an all male engineering team. Building a diverse company is like building a product - in order to attract the customers (candidates), you have to demonstrate that you’re diverse from the start, from the inside. I’ve seen companies that are Series A/B that are composed mostly of white people or mostly men (companies that are fully remote and can hire from anywhere, or do not match the geographic racial/gender region makeup that they’re located in). At this point, it definitely throttles hiring and limits the talent pool that will want to work with you.
  • I read on twitter that somewhere, a VC was talking to a founder and the founder said that they don’t have time for diversity, and that diversity is hard work. The VC responded that they’re not afraid of hard work. As a founder - you’re already doing a hard thing, and that takes hard work. Don’t be afraid to put time into diversity, early on.
  • I take responsibility for my mistakes. Sometimes, candidates fall through the cracks - and later follow up with me weeks later. There are times where I haven’t made my criteria tight enough, so I couldn’t give candidates a proper timeline, and this also impacted the experience that they had. I was unfair to them, admitted to them that I was unfair to them, and apologized. Be humble.
  • Be honest with candidates. Give them the hard news if it’s hard news, and give them good news when you have good news. Try to be encouraging and empathetic, the job hunt is so, so difficult.
  • If you repeatedly get the same (wrong) answer from candidates, you may be asking the wrong questions. Every part of your interviewing process should be experimental to see what works best.
  • Just be nice and a good person. We’re all out here trying to make our change in the world :)
teresaman's profile thumbnail
Wow, this is such a thorough and comprehensive guide Samantha, appreciate you tenfold for sharing so many tactical tips, learnings, and strategies in scaling a company ♥️
SamanthaChai's profile thumbnail
Thanks for your feedback Teresa! I noticed a lot of my founder friends were reaching out to me for advice re: hiring, and there were not many resources on how to organize hiring - rather, they focus on things to look for in a candidate. I'm glad you think it's useful! :)