Hello and welcome back to the Founder to Founder newsletter!

The way I approach hiring has changed quite a bit since starting OpenPhone.

Before becoming a founder I worked as a Product Manager at Vidyard. Being in the role, I had almost no hiring experience.

Sure, I had to opportunity to hire three amazing interns during my time there, but that’s about it.

But the stakes are a lot higher when you’re hiring full-time for your own startup—especially when those first few hires can make or break your company.

Since starting OpenPhone in 2018, I’ve directly hired 24 people.

(Tbh, I'm a little surprised it’s only 24, I expected this number to be a lot higher 😅)

There was a lot I didn't know when I first started building the team at OP— lessons I wish someone had told me.

So I decided to reflect on my experience so I can share my learnings with you. I sat down and went through every single hire I made—all 24 of them. I looked at everything: what went right, what didn't, and what I wish I knew before.

I created a scorecard to break down what actually mattered in each hire. There were 5 lessons that stood out to me.

Let me show you what I found.

📒 DEEP DIVE

What I wish someone told me about hiring as a first-time founder

Plus my hiring scorecard

My hiring scorecard

First, I want to walk you through how I assess my own performance as a hiring manager. This will help give you context as I get into the 5 learnings.

For each of the 24 people I’ve hired, I’ve noted the following:

Were they the right hire?

➤ Yes - they successfully did the job they were brought on to do

➤ No - they weren’t successful

Were they hired as an individual contributor (IC) or a leader?

Was I familiar with/had I done the role I was bringing them on for at the time of hiring?

➤ Yes - I did this job or was well familiar with it

➤ No - I didn’t do this the job at OpenPhone in a meaningful way

Noted the source of this candidate:

➤ Inbound - they applied

➤ Referral - referred by someone we knew

➤ Outbound - we proactively reached out

The results

1) My overall hiring success rate is 66.7% which is much higher than I imagined in all honestly.

2) Not surprising, but hiring leaders is a lot harder than hiring ICs, so my success there was 55.6% vs 73.3% for individual contributors.

3) Job clarity (aka actually knowing what you’re hiring for) leads to more successful hires. When I was familiar with the role I saw an 80% success rate vs just 44.4% for those that I didn’t know as well.

Shocker—the better you know the job, the higher your chances of making the right hire 🙂

4) Inbound has been amazing for the roles I’ve hired, better than referral (a little surprised here!) and outbound.

The only way I can explain this is that when your company is very early, you need people who are super bought into the mission.

Of course, you can find those candidates who are bought in through referrals and by sourcing them yourself, but you get a lot more of that with inbound applicants. They're actively raising their hand to join your company.

As I reflected on my own mistakes and learnings, I realized there are a few key things to avoid.

Now let's get into the five things I definitely wouldn’t do again when building a team.

My top 5 hiring lessons

1. Don’t hire without knowing the ideal candidate archetype

Based on my own data, knowing the job you’re hiring for improves the odds of success by 76%.

Crazy, right?

When you don’t know the job you’re hiring for, you’re basically hoping that luck is on your side.

But the key isn’t knowing all aspects of the job, it’s figuring out what's truly critical for this role and your company in the next 18 months and digging for evidence of this during the interview process.

This allows you to create a clear candidate archetype.

This idea clicked for me when I worked with Executive Recruiter Amber Mederos Weinberg, who introduced me to the concept of "archetypes." Here's how she explains it:

What I love about Amber's approach is how she looks at candidate's experience: everyone has a major and minor discipline.

For example, say you’re looking for a Head of Marketing for your startup.

You’re creating a brand new category and need to do a ton of education in the market. You probably need someone who’s an experienced product marketer.

But you also expect this person to build a repeatable growth motion and invest into performance marketing to get the word out. This means you might be looking for someone with a major in Product Marketing and a minor in Growth Marketing.

That’s a much more specific profile (or archetype) compared to just looking for a marketing leader. As a result, it’ll increase the odds of you making the right hire dramatically.

Now, how do you figure out the right archetype for role you're trying to fill?

Here are some things I’ve done in my hiring experience:

1) Get hands-on with the team and spend time talking about problems we need to solve.

2) Work with advisors who have expertise in the area we’re hiring for to get their take on the candidate profile. (Note - this only works if they have sufficient business context)

3) Bring on recruiting partners with experience in hiring for similar roles.

4) Build an interview process around the key traits, ensuring interviewers are aligned with the focus areas.

5) Talk to founders who’ve successfully hired for this role or just made a lot of similar hires.

2. Don’t ask folks for their “30-60-90” plan

I used to love asking leadership candidates for their 30-60-90 day plan.

Now I realize it wasn't helping anyone—the answers were too vague for me as a hiring manager, and candidates were often missing real context about our business that was needed to make any valuable recommendations.

Instead, I've found it's much more valuable to focus on one specific key challenge they'll have to tackle in the role.

Ask them how they'd approach solving it—that will show you exactly how they think and work, without any of the fluff.

Let me give you two examples of how this works in practice.

1) When hiring our VP of Marketing Jordan Hwang, we wanted to understand how he’d think about the challenge of acquiring and serving larger customers.

In his answer, Jordan showed the depth of thinking about the problem and asked lots of key questions, engaging everyone on the panel in a thoughtful discussion.

At the end of the day, something like the journey up-market requires intentional collaboration between Product, Sales, and Marketing and that’s exactly what he showed in his answer.

2) When hiring our first Product Marketer Jordan Simas (yes, also Jordan!) back in 2021, we asked him to draft a “we’re raising our prices” email.

We didn’t plan on raising prices at the time, but thought that it might happen eventually and it would be something that the Product Marketing Manager would be tasked with.

I knew that our PMM would have to write a lot of different emails so thought to write the exercise prompt based on one of the harder ones.

What stood out in Jordan’s answer was that he clearly explained any assumptions he made right away and then his principles for sending an email like this.

It helped that the email was well-written with attention to detail and fit OpenPhone’s tone of voice.

The big takeaway? Instead of asking candidates to tackle every challenge they might face, pick one.

3. Don't overlook founder content when hiring

I’m surprised to see how much better “Inbound” worked as a candidate source vs “Outbound” and “Referral” 🤯

Even if you think you’re hiring for a very specialized role, you never know who’s going to see your JD and throw their hat in the ring, so don’t forget to promote the roles you have open on social media and relevant online communities.

For example, this post from last year when we were looking for our Partnerships Lead was one of my top posts of the year & lead us to Juraj Pal who ended up joining OpenPhone shortly after.

This is one of the reasons why I've been focusing on posting more often on LinkedIn, and now launching this newsletter. Content is a magnet for great-fit candidates.

4. Don’t skip on references

It’s tempting to skip this step, especially if it’s someone you’ve sourced yourself or someone who came in as a referral. But asking for references is the easiest way to improve your chances of making the right hire.

When I share this advice I typically hear “But these are all formal references—nobody will say anything less than stellar.”

While folks tend to be positive, they also won’t lie. With the right questions, you'll learn a lot about who you're about to hire.

Here are 6 questions I ask when speaking with references:

1) Tell me more about the way you’ve worked with this person (an easy way to get the conversation going and confirm details).

2) Where would you put the candidate on a scale of “the best person I’ve worked with”? Top 5%? Top 10% Top 25%?

• If the answer is anything lower than the top 10%, follow up with “What did the folks who you’d rate as top 5% do that this person didn’t?”

• If the answer is top 5/10%, follow up with “What did this person do that others who you wouldn’t rate so highly didn’t?”

3) What were this person’s biggest accomplishments in their role at {company}?

4) What are the kinds of questions or problems you’d go to this person with? (a much better way to understand their strengths vs asking directly)

5) [If talking with a former manager] What kinds of feedback did you share with this person? How did they take it? What did they do as a result of it? (understand their ability to improve and act on feedback)

6) [if talking with a peer] What’s something you think this person can do to grow in their role? (understand areas of growth)

5. Don’t fall in love with a candidate prematurely

In the early days of OpenPhone we didn’t get many inbound applications and had to fully rely on sourcing candidates ourselves.

Any time a candidate responded to outbound outreach, it was such a thrilling moment—especially if this was someone with big brand name companies on their LinkedIn.

I have to admit, a lot of those conversations quickly turned from interviews to me “selling” them on joining OpenPhone.

Remember how I mentioned that the best candidates need to be bought into the mission? Well, having to 'sell' them on the company continuously doesn't quite match that.

Many times, in the process of pitching the role to a candidate, I didn’t put in the time needed to see if they actually were the right person for it.

Losing sight of this can cloud your judgment as a hiring manager. But there's no real 'framework' to fast-track learning this lesson.

It’s less about the templates or questions to run through and more about keeping the discipline to know that hiring is a two-way street.

If you sell someone too hard and it’s not the right fit for them, you might end up in a worse place than where you started. 😅

So the goal isn’t to have to keep on selling but rather explore if the fit is there on both sides.

Final thoughts

I'm going to be honest. Although I have more experience with hiring now and have learned a lot, I still find it the hardest thing about being a founder.

Every time I reflect on my experience and keep learning more about hiring, I realize there’s always more to discover. It’s a constant process of refining my approach, and I’m sure I’ll be back again to this topic with even more lessons learned. 😅

It’s never a one-and-done thing—just when I think I’ve got it figured out, I realize I don’t. I'm sure I'll have an updated version of this newsletter one year from now.

But that’s the fun of it, right?

Until then, take care 👋

Daryna

ps - we’re hiring a Product Marketing Manager! You’ll be our second Product Marketer and join at a very fun time. We’re shipping a lot and have some game-changing stuff in the works 🔮