Profile: Kushal Choxi, from First Deal to Sales Leader in Months

I sat down with Kushal to talk through his Clipboard journey - starting in New Verticals, becoming an Account Executive in Core Sales, and then quickly rising to become one of our Sales leaders!

Hey Kushal! What do you do here at Clipboard?

I’m a Strategic Account Executive on the Sales team, where I focus on our biggest corporate accounts. My job is to grow Clipboard’s footprint across the nation by working with high-level stakeholders - everyone from Directors of Nursing and Administrators to COOs and CEOs. I help them understand how our product is best-in-class, can solve their staffing needs and ultimately make their lives easier.

And what did you do before Clipboard?

I feel like I’ve had a couple of different lives before Clipboard. Right after college, I moved to New York and worked at JP Morgan in the Private Bank for about four and a half years. I was mostly behind an Excel spreadsheet, managing balance sheets for ultra-high-net-worth individuals. To be honest, I felt like I was just making rich people richer and I wanted to do more with my time and make more of an impact.

I knew I wanted to join a startup, so I joined a small, seed-stage company in the healthcare space. That was at the time the investment market shifted to chasing profitability rather than growth at all costs and the company ran out of funding, so I found myself looking again. I wanted something that had both an entrepreneurial, startup-feel and the financial firepower to make big bets. And through the YC website I found Clipboard.

I was immediately drawn to the mission of helping people move up the socioeconomic ladder. I come from a low-income household and actually qualified as a CNA myself (Certified Nursing Assistant, one of the core license types we fill shifts for!), so that mission really stuck out to me. Clipboard hit all my criteria: it was a top YC company backed by Sequoia, it was profitable, it had a great mission, and the team was incredibly impressive (one of the Co-CEOs, Bo, had sold his previous startup to Blackrock).

Amazing, tell us more about your experience as a CNA?

My parents were CNAs, and in high school I took a medical careers class that offered vocational training. After about six months I got my CNA license. A lot of people who took the class went on to do other things in healthcare - I thought I was going to be a doctor, like many Indian parents hope for their kids!

That experience gave me so much perspective on how incredibly hard the job is and what really happens in these facilities. They are often short-staffed which puts patient care at risk. You’re helping with movement, changing, and everything in between for people’s loved ones. I have a huge amount of respect for CNAs. They take so much pride in their work but are often under-appreciated and understaffed.

No doubt that’s been super useful for empathizing with our customers (and you’re not the only CNA here - our Co-CEO Wei followed in your footsteps, getting her license so she could work shifts through the Clipboard platform!). Jumping back to when you joined Clipboard, how did you find the application process?

Honestly? When I first looked up Clipboard on sites like Glassdoor, I saw a bunch of “this company sucks” reviews. I thought two things: wow, this company might be a scam or… they just hold a really high bar and it’s going to be great right? Two very different extremes! So I decided - I’m going to be curious and go through this process myself.

But I didn’t nail the process initially! The first step was a case study which I didn’t do a good enough job on. But after my first interview I went the extra mile and created a detailed list of prospects that I’d target if I was in the role, which led to a second interview and I got hired quickly after that (I guess I treated it a bit like a sales process where I showed my value and followed up).

Now I’ve seen the hiring process from the inside and one of the things I love is that we don’t care about resumes or the places you’ve worked before. That’s actually why we use case studies - we want to see how well you can actually do the job.

How has your role evolved since you joined Clipboard?

It’s been quite a journey. I started on the New Verticals team, which was like a startup within a startup. We were tasked with launching new businesses within Clipboard beyond our core long-term care business. I was focused on building a marketplace for locums (medical professionals that cover for absent staff), especially anesthesiologists and emergency medicine physicians. It was exciting because there wasn’t much structure - it was a small team of us figuring out the market, the strategy, and what to build. It was my first taste of Clipboard giving team members an incredible amount of autonomy and trust.

I did that for a while but we quickly decided that it’d be better to put talented people in areas we can scale a lot faster, so I moved over to the core Sales team (focused on bringing healthcare facilities into our Long Term Care staffing marketplace). It felt like joining a different company! Overnight I went from scrappy spreadsheets to a well-oiled machine with established systems and support. It was a great testament to how, once we validate an idea, we have enormous resources to go after it.

On the core Sales team, I started as an Account Executive, managing a territory and owning the end-to-end sales process. After about six months, I graduated to a Corporate Account Executive role, where I began managing significantly more complex deals with multi-facility corporates. Now, I’m a Strategic Account Executive and am trusted with our largest, most important corporate accounts. I spend my time speaking with and selling into C-suite stakeholders but my role involves so much more beyond simply closing revenue. I coach our Account Executives, shape deal strategy, partner with Warren (our CFO) and the rest of our leadership team to help steer how Sales operates. In many ways my journey is a good illustration of the typical Clipboard growth story - if you take extreme ownership and work hard, you will get opportunities here faster than anywhere else. I’m just one example but there are loads - this kind of growth happens across Clipboard all the time.

When you talk to prospects and customers, what stands out to them about the product?

We have the best Product team and the best product, hands down, and that makes my job a lot easier. Because we always have the solution to our customers’ problems.

So when I hear the horror stories from prospects about reliability and accountability with other staffing agencies, the Directors of Nursing working 80-100 hour weeks, desperate for a solution… I know we can solve their problems and genuinely change their lives. We’re not just filling shifts - we’re giving people time back to spend with their kids, we’re helping people get their lives back, no more sleepless nights. That’s incredibly powerful.

And when I do hear new issues from customers I know I can send a few Slack messages to our Product team and they’ll be working on a solution immediately. No bureaucracy at all.

What are the best things about working on the Clipboard sales team?

Honestly the best thing about working at Clipboard is the autonomy and responsibility you’re trusted with. From the time I was first hired to now, I would never have gotten this level of ownership and ability to make decisions at any other company.

That’s the first thing. Second, you get to work with the smartest people, we have a genuinely world class team. Even though I worked in banking, I still think Clipboard has the smartest people I’ve ever worked with and that’s across the whole business. The level of thought they put into things is just amazing. And everyone believes in our mission to move our customers up the socioeconomic ladder by giving them more opportunities to work.

Lastly, we like to have fun. We do a lot of team offsites (next one is in New York in a few weeks!) and I also get the chance to hang with the team regularly at conferences. I’m actually heading to Las Vegas this weekend for a conference. There are also lots of chances to hang with other Clipboarders in real life (and we each have a $50 monthly budget to spend on doing stuff with anyone else at Clipboard, e.g. dinner).

So those are the things that really stick out to me. If you’re looking for a challenge, want to grow in your career, and want to work with a world-class team that has the potential to transform not just healthcare staffing but literally all labor markets, I can’t think of a better place to be. I’m super hyped!

And finally, what do you do for fun outside of work?

I love to hike, I love to get outdoors - that’s my big thing. Another great thing about Clipboard is that it’s a remote company, which gives so much flexibility. I just moved to Chicago, I’m loving exploring the city and I travel a lot for both work and fun. I also love watching football plus I’m planning my wedding right now! I’m getting married in India in January and everyone at Clipboard’s been so supportive and happy for me, I can’t wait.