Remote Work Interviews

Owl Labs (OL): Tell me about how you got to where you are in your career today.

Ben Aronowicz (BA): It wasn't one specific step that brought me to where I am today. I feel a lot of my success comes from me continuing to say 'yes' to opportunities that looked challenging to me. It's natural for people early in their career to worry about their current job title or salary, and while I did too, and money is a real concern, I've found it's more important to focus on taking pride in your work and taking on challenges that propel your advancement.

For me, my first job out of college was as a janitor at a computer store. I was the best janitor. The toilets were actually clean! From there, I kept saying 'yes' to things that would challenge me. In my first year at the store, I received three raises that brought me all the way to $12.50 an hour, and I was promoted to Store Manager. This was a 30-person business, and I was about 24 years old. Suffice it to say, I learned a lot.

OL: You're the Head of People Ops at Thinkful. Did you start at the company in that role, or did you advance into the position, as you did in your first job?

BA: When I joined at about 25 people, we didn't call it People Ops. We had a large team of contractors, and hiring and supporting that 300-person remote team was my first job at Thinkful. It was part customer support, part people operations, and part recruiting. Then, I started hiring for the full-time team internally. I hired for us until we reached about 80 people and then we started growing the recruiting team, and now, the People department is a 10-person team focusing on recruiting, traditional HR, and People Ops.

OL: What's the mission of Thinkful, and how does it map to you?

BA: Thinkful's mission is to bring high-growth tech careers to ambitious people. What makes our mission so unique, from a recruiting perspective, is we're very human-centric in how we deliver that education. Our course leverages one-on-one mentorship and provides a network in your city, on top of the immersive online curriculum, which makes us less of a SaaS company teaching you to code and more of a career accelerator partnering with individuals to achieve success. We are always hiring for people who are excited to help others access more meaningful careers.

For me, when I moved back to New York, I got a job at Apple working in sales. I moved into a role where I was assisting new hires with their training and facilitating employee learning and development programming. My favorite part of the job was when people would come up to me, months later, telling me they'd received a raise and thanking me for my help along the way. Helping these people go from $12 to $18 to $40 an hour was really rewarding.

What I like about Thinkful is we have that same impact on someone's career mobility here. We have students going from $40,000 a year to $100,000 a year, or at least getting on a track toward that kind of earning potential, after completing our programs, and I love supporting that.

OL: You provide students with tech, coding, and data education, right?

BA: We teach courses on web development, design and product design, data science, and data analytics. We also offer a hybrid learning experience. If you live in a tech hub, there's a local community you can tap into to further your education and for networking opportunities. In general, there's an online learning platform and different components of support available to you. We use the phrase "360 support" because there are group sessions — basically video conferences where you can receive live help, Slack support, mentorship, career coaching, and more. Plus, a program manager helps to guide you through pacing, motivation, inertia, and life blockers that can come up over the course of one of our intensives.

This assistance can be so powerful. Trying to make a career shift is tough enough for students, let alone moving to a new city where they don't have a community or friends yet. There are so many stressors that come with moving, not to mention the isolation that comes along with it. Now, our students are able to move to a place where there is a local community, with people in the same program as you, coming to an event is almost like you're going to meet your class and alumni network.

OL: Thinkful offers a hiring guarantee to students, is that right?

We do, and that's rare in the education field. That's one of the main reasons students come to us. Yes, they want to learn the skills, but what they really want is a job in tech. If we can't guarantee that, then what are we doing?

From an organizational perspective, this has been huge, because offering a job guarantee is hard. We need everyone invested and on the same page in order to make that happen — from our admissions team that helps students select the best course to our careers team which builds relationships with employers to help place graduates.

OL: Tell me about the people who work at Thinkful. What's the breakdown of remote versus co-located people working in New York?

BA: In terms of the team, we value mission and value alignment when we hire people. It's a huge factor for employee retention, especially on a remote or hybrid team, and we look for a strong growth mindset as challenges will evolve for every employee.

Twenty percent of us are still based in New York, and the rest of the team works remotely. There was a point when one of our founders wasn't excited about remote teammates, because he didn't think it would be as effective. Then, one of our engineers started working remotely, and she crushed it. He saw how she remained incredibly effective, and he started to believe it could work for the rest of the team.

When our local strategy with our product started succeeding in three mid-sized cities, and then in nine cities, we started hiring people on the ground. From there, someone would refer someone who happened to live in say, San Diego and we'd say, "Well, we already have one person in San Diego" and hired a second person. As our local experience grew, we targeted more and more places. Now, we're just as excited about hiring someone in rural America as we are in a city where we already have several remote employees.

OL: What kind of support would you provide to two remote Thinkful employees who might not otherwise know each other but both live in San Diego? Do you get them together?

BA: Generally, in your first week, people in your city will take you out for food and drinks to meet the local team. This will vary depending on the size of the local team, but we encourage (and pay for) folks to meet up. 

We offer a co-working space stipend as one of our benefits, which helps consolidate where our remote team works and helps those two people (and later others) meet and work together. Another goal of offering coworking stipends is just getting people out of their houses, so they don't go stir-crazy working from home every day. When people go to more meet-up style events, and leveraging free workshops and happy hours, they combat loneliness, which is real for remote employees, and build their local networks. It's also helped us with referrals, meaning we've hired people who worked in the same co-working space as a current employee.

New folks also need to meet the larger team and I see our role as providing structures for them to have meet and have face-to-face conversations with each other.  Beyond one-on-ones over video with your manager, we use a Slack integration that sets-up bi-weekly dates to meet others in the company. This time can turn into fascinating talks and bonds that drive engagement across the company in different ways. I call these structures benefits because we're telling employees to take the time when they'd normally be working to go out and meet others.

OL: Along those same lines, how have the perks at Thinkful evolved since you've shifted from being primarily co-located to now being mainly distributed?

BA: One of our first benefits was everyone in the New York office receiving a MetroCard for life. As we moved to remote, we added the co-working space benefit I mentioned.

We also went from 30 to 120 employees so we had to define and revamp most of our policies. For example, we went from offering parental leave as a part of our unlimited PTO policy to building a more defined and separate parental leave policy that removes any negotiation from taking the time one needs.

Beyond scaling, the biggest change was trying to be more intentional about our offerings in general, so we focused primarily on wellness and connection. Sure, Thinkful could pay for everybody's electric bill or their internet bill if they work from home, but we don't want people to only work from home every day, so we pick benefits that encourage people to build networks, and be healthier.

For our health goal, the first step was providing the Headspace app. Just get health in peoples' hands. Building your network starts with us having a local community and, of course, the co-working space benefit. We are excited for 2020 and to continue selecting benefits with increased intentionality.

The questions we're thinking through when it comes to future benefits include: How do you make wellness something you do together as a remote company? How do you get people to get out of their 'caves', out of their homes, and get them out in the world meeting people more?

OL: How do scheduling and communication work when employees are distributed across so many different time zones?

BA: One big part is sharing our calendars and keeping them accurate all the time. We value urgency and tell the team to schedule first and ask/inform second. People can reject the invite as needed, but by and large this works very well. Every recurring meeting has an agenda document that people can add to and follow along during the meeting and look back to later.

Instant communication tools, like Slack, can be both a blessing and a curse. Notifications can make people think something must be very urgent if everyone's Slacking you. At the same time, you can think, 'that's not important' when it is, because no one's next to you telling you 'I'm stuck.'

A general culture of trust is a must on a remote team, because you don't see each other working. People are going to get to things in the order of priority that's right for them, and you must trust that they're prioritizing their highest-leverage work.

OL: Remote work can still mean a rigid schedule for people without team-wide understanding like what you describe.

BA: For us, if you need to go to a doctor appointment, you put it on your calendar, and you go to the doctor. There's enough buy-in and trust that everyone is doing the work they need to do every day. We think it's important to offer that level of trust and autonomy to the team. The flexibility of our remote work policies and the distribution of our employees across different time zones means our employees are able to set the hours that work for them. Ultimately, they're measured on outcomes, not time spent at a desk.

For the more complex scenarios we have policies, but by and large, treat folks like humans all the time, and consider the precedent you would set. Ultimately, if I know a team member works incredibly hard, and they want to take three weeks off to go to China, I don't care. I know that person is going to come back and deliver. Let's just ensure their manager planned for it.

OL: Is Slack a big employee engagement tool at Thinkful?

BA: Definitely. We have a Praise channel on Slack where people can shout each other out for helping them out or hitting a goal or other notable things like that. More than half of the people at the company have praised someone else in the last six months. We also have a First Day channel where we announce all of our new hires and role changes. Each new hire is announced in the channel with a brief explanation of their role and their answers to a bunch of questions about themselves, such as what brought them to Thinkful, their favorite food, their ideal superpower, etc. It's a fun way for people to get to know each other and have a better sense of why we hired that person. 

In addition to Cats and Travel, we have a Slack channel dedicated to manager growth. We have someone on our Careers team who holds a weekly manager sharing meeting, where all-level managers can show up and ask for advice. Everyone gives fake names for their direct reports, and it's an open place to share thoughts, frustrations, and advice. If you're a manager and you don't know what to do, you can talk to others in leadership and someone from the people ops team in an open forum, and continue the discussion in the Slack channel, too.

OL: What are some strategies you've learned for management, collaboration, and communication that are particularly helpful for hybrid teams? How do you maintain that balance when some people are together every day and some people aren't?

BA: The short answer is, it's really tough. Most of the time, you're doing it in a unique way that may or may not be the right way to do it. It's not possible to do it perfectly – that's not the bar hybrid team leaders should hold for themselves. Miscommunications happen everywhere, and those instances can be exacerbated with a hybrid or remote team.

We opted to not build our team's communication strategy to be for a hybrid team, because then you have to do everything twice. We minimized the overhead by building all of our processes and communication strategies assuming everyone works remotely. These processes can be tweaked for colleagues who work together in-person, but it's important to do the legwork for remote employees first.

At some point between 60 and 100 employees, it became less about making sure everyone knows everything about the company, and more about how teams work together and help one another. Getting the team to hear the same thing to align and the things they need to know to do great work requires a constantly evolving strategy.

It's important to know some things deserve face-to-face and one-on-one interactions with people. All of us hold weekly one-on-one video meetings with our managers and reports because of it. Sometimes getting off Slack and onto a video call if wires are getting crossed is crucial. Sometimes a decision can't be made via Slack or email, or is worth sharing with your team in a live setting where people can ask questions and be heard and give feedback. Hiring leaders who have confronted this is a must.

Hybrid team management isn't that much different from co-located team management, but you can't do certain things, so planning and thought are required. When your team can't celebrate wins in the traditional way, you need to be thoughtful about ways to translate that same sentiment remotely. At Thinkful, we still do team-building and we still celebrate wins, but it looks different than you might assume. If you're at a recruiting agency, you hit the gong when you made a big hire. Here, that moment has to be a GIF of me hitting a gong that I bought and then filmed and then uploaded to Slack to post when we hit goal.

OL: How does the recruiting process vary for employees you're hiring for remote roles versus those who need to be at headquarters?

BA: We don't hire any role with the restriction that they have to be based in HQ. It can be a preference, but it's never a requirement. We have C-level people in Seattle and Kansas City, so that policy applies to everyone. Hiring when we don't care about the location of the candidate speeds us up, shaving more than two weeks off of the average candidate search process, depending on the seniority of the role.

You can choose to have a compensation strategy that lags behind the market in an area of your business that you want to grow aggressively because you offer remote work as an option, which can be a good strategy for a growing business. When people don't have to commute, pack a lunch, or spend 400 minutes of their week commuting, candidates can get so excited to the point that they'll take a small pay cut for that flexibility and improved quality of life.

On the candidate side, you need to hire folks with a high degree of autonomy who will drive to find -- and eventually, provide -- answers on their own. These people tend to not worry about hopping on a call at 8 p.m. once in a while in order to meet with a person who only frees up on the West Coast at 5 p.m. their time. You're looking for people who value urgency and know how to balance their schedules so they're able to work effectively and live their lives.

If they're coming to their manager to review every email they send or need step-by-step directions on how to grow their skills, they're probably going to be unhappy at a hybrid or remote company because they're going to spend a lot of time in lag waiting for answers. Being able to self-manage when you have the authority and ability to work independently is crucial for the pace we work at. We're looking for people with intrinsic motivation and drive to find answers, solve problems, and connect with others.

Candidates also need to place a high value on intellectual honesty, whether they work remotely or in New York, because a lot of public conversations happen here on Trello boards or in Slack. Everyone at Thinkful gets feedback in public on their work, so our recruiting team has to evaluate how professionally you can both deliver and receive feedback across public channels.

OL: Remote companies talk about the importance of writing effectively and clearly, but your point about being mindful and giving feedback in a way that's constructive while not throwing anyone under the bus or getting defensive across these public forums is an interesting one, too.

BA: You need to be able to accept when that doesn't happen in grace, because you're working together five days a week for 40+ hours, and someone is going to have a bad day every now and then. Maybe they're tired, they didn't eat lunch, or they're a little more abrasive than you. You can take it as a personal slight and get frustrated or defensive. You have to be able to take those moments and say, "They're not mad at me, let me get to clarity on the issue" because it's just going to happen. We're only human. There's far less context when people work remotely, and people need to be not only proactive communicators, but proactive context seekers too.

OL: How can start-ups effectively build a recruiting program that's beyond sourcing referrals and scouring LinkedIn?

BA: You need a model of how the organization is going to take shape to meet its goals in order to have intelligent conversations around your hiring needs. Certain departments support one another. Recruiting is one, Product is one, and Engineering is another. If you grow the customer support team by 20x but the engineering team by only 2x, then everyone suffers when the engineers get inundated with customer support tickets and the customer service team frustrated by lack of support. Without a thoughtful approach, you'll overload your existing employees to the point where they burn out, and eventually leave you.

Another painful mistake managers make is they think a new hire in Q2 will drive results in Q2, when they likely won't, so it's important to have these growth plans in advance and proactively set expectations and revisit them as things change.

Once you start building this process, you can turn it into a roadmap where you say, "In order to scale at the level we want, we have to hire at this pace for X many roles in each department." You should be cautiously pessimistic when you first project this, but it gets more accurate with data and time. Use a shareable document or Google Sheet so that everyone can see the thought process and data behind headcount decisions – it should be transparent to the whole company, not just the recruiting and leadership teams. This transparency drives referrals and internal movement.

With a process, you need to pick a leader for recruitment, and you need to empower them to maximize their impact. They must report to a Founder, and be able to spend money to go faster.

I often heard, "Don't hire recruiting coordinators, they quit as soon as they learn the skill-set", so I hired contractors to do all of my sourcing initially. Your recruiter shouldn't be spending hours sourcing candidates – they should be managing contractors doing it for them to meaningfully free up the recruiter's time as a decision-maker and process builder who raises the bar for the company.

You need to pick a recruiter who can build trust with others at a high level and is frugal but values fairness and fidelity. I want to go home at night and know my team's salaries are fair, but affordable. This person needs to care about the company's budget while able to balance it with the enthusiasm of the candidate and the needs of the hiring manager and the team.

Finally, growing companies can get a ton of value by leveraging referrals. People always think you have to pay employees for referrals, but that isn't necessary. We don't pay a dime for employee referrals, and we made more than 12 hires in the last six weeks from referrals. I believe people should refer others because they want the company to succeed, and if they're doing it for $75 at your 100-person company, that's a bad sign. They should want to do it because they're the right fit. To build up a referral funnel, recruiters should hold sessions with employees, showing them what to look for in their LinkedIn and Facebook networks. Eventually, pay your people for their referrals, but I'd wait for when it's culturally the thing to do anyway.

We have a Slack channel where, every time someone makes a referral, a dancing rainbow corgi emoji pops up to acknowledge someone made a referral. It's silly, but it works – it helped double employee referrals.

OL: What do you love most about your job?

BA: The fun part of my job is that I feel like I hired the team that I now have to take care of. My level of responsibility and motivation and engagement with my job is literally tied to people I made a career promise to – and I made that promise to 100 people. "You're going to have a great time with this company and we're going to help you succeed." That turns out to be the most fun of this job – from bringing new people on to thinking about how to help people get to the next level in their career. Progressing in my role to see how team members and the company grow is so fun.

If anyone reading this is wondering if a job like mine is right for them, I never thought I'd go into HR or people management. I actually said I didn't want to recruit anymore to my founders. But it's a very interesting space with a ton of best practices that you can research and copy and adapt to your team and tons of emerging trends to reimagine. There's a lot of green space in People Ops and HR where you can be progressive and try new strategies. It's an interesting time and an exciting opportunity to work with people right now. In that way, the mission of my job is my own.

Key Takeaways

1. To build a successful recruiting program, outsource candidate sourcing via contractors and referrals so recruiters can spend as much time as possible screening candidates and working with hiring managers.

Ben advocates for this strategy to maximize the value of recruiters' time so the bulk of it is spent interfacing with internal colleagues and external candidates to close the hiring loop faster and to keep recruiters engaged at work.

2. Choose benefits that align with your company and employer values.

Ben cites wellness and connection as the two primary values Thinkful seeks to achieve with its benefits offerings, and believes that the benefits companies offer should align with what company leaders want for their employees and their community as a whole.

3. Hybrid companies shouldn't try to build a hybrid company culture.

Ben believes that, instead of attempting to build a hybrid team culture that's inclusive of both remote and co-located employees, companies should instead focus on building a culture that's designed for remote employees that can be tweaked for co-located team members. That way, Ben explains, instead of building two distinct cultures, processes, and rituals, you'll build a culture that works for everyone, no matter where they're hired.

To learn more, read our latest interview with Tracey Halvorsen, co-founder and Chief Visionary Officer of Fastspot next.