Interview with Sagar Jajoo, First PM at Truework

This article is part of a series revealing the stories of early employees from the most successful tech companies of the past few years. You’ll walk away having learned about what these individuals experienced, what they wish they knew, and the advice they’d give to others joining high-growth startups. Key takeaways are at the top and you can find the full interview below. 

This interview is with Sagar Jajoo. Sagar was the first Product Manager and is currently a Product Lead at Truework, a platform to help banks and lenders verify income and employment data. Truework recently raised a $50m Series C. Below is an edited version of a conversation he had with us here at Compound. 

Note: If you’re looking for an all-in-one solution to manage your personal finances, Compound can help. We can help you diversify concentrated stock positions, optimize company equity, plan asset allocation, and more. Request access here and we’ll be in touch.

Key Highlights

• On building trust with the CEO to lead product – “One big part was deeply understanding where the CEO wanted to take the product both over the next 3-6 months and the next 3-5 years. Early on, the CEO and the CTO were both still involved in the day-to-day – they would sit in on planning meetings and chat with the engineering manager to make sure everything was going okay. But as soon as they realized things were stable and that I was able to run things pretty independently, it opened them up to work on other priorities. I gave them leverage. 
• On joining as the first PM – “A founding product manager role was really exciting but it can be sink or swim. I realized that the fact I was nervous for the opportunity was the reason I needed to take it - I knew it would be an incredible opportunity for growth (which ended up being the case). I was also excited to define and cultivate a product team culture and establish the norms for how Product operated.”
• On Truework’s market opportunity – “Lending is still fraught with friction. For a basic lending process, all you really need to do is assess and mitigate risk. And credit, asset, income, and employment are the most common data elements to do that. Credit and asset data is quite easy for lenders to access but income and employment are not. In talking with lenders, I realized that there was one large solution, the market hadn’t innovated in a while and it was quite expensive.”
• On Truework’s core values – “We have four: be resilient, value diverse perspectives, put consumers first, and design the future. A lot of companies have values but don’t really live them everyday, but at Truework they’ve become part of our everyday culture - in interview processes, hiring panels, all-hands, etc.”
• On a major challenge for Truework – “The biggest moment of doubt I had was about a quarter after our largest customer by far at the time onboarded, as that same customer churned from Truework. We had doubled revenue overnight, were really excited and had shared the news with investors, but now we had to explain why our revenue graph had a steep downward slope. Emotions ran a little high. But what I was most happy about was how the team overcame that challenge.”
• On learning about startup equity – “If you don’t know about equity yet, think about it this way: what’s the higher ROI, spending an hour or two to learn about tax implications of your decision, or spending it on your day job? It’s far higher to learn about your equity. In your job offer you might have the option to negotiate a higher cash salary or higher equity, and having the right information can be worth five or six figures later on.”

How did you first hear about Truework?

I first heard about Truework while working at my last job (Blend) on their product team. I’ve always been a very curious individual and wanted to treat my jobs not just as a way to get work done, but as a way to learn about an industry, learn about challenges that customers have faced. 

While I was at Blend, I got the chance to work with some of the biggest lenders in the country (like Wells Fargo) on digitizing their entire mortgage and consumer lending origination processes. Through that, I got to understand all the complexities of what it takes to underwrite a home or consumer loan – all of the parties involved, the documents, data and regulations. One of the biggest problems lenders face was actually verifying income and employment data. 

At its core, a lending process is about assessing and mitigating an applicant's risk. And credit, asset, income, and employment are the most common data elements to assess risk. Credit and asset data is quite easy for lenders to access but income and employment data is not. In talking with lenders, I realized that there was a large incumbent who hadn’t innovated in a while that offered a solution that was quite expensive, and no viable alternatives available. 

Blend was looking for innovative partners to work with on the problem of simplifying and complying verifications for their customers. They happened to talk with Truework’s founders – the first time I heard of the company was from a summary of Blend’s partnership team. The notes were pretty positive and they seemed excited to work with us. 

A few months later a close friend of mine mentioned that a really cool early-stage fintech company was looking for their first PM. When I heard it was Truework, I was happy to take the call. That’s how the process began. 

What made you want to join Truework?

When going through a job search, I think everyone should have a set of criteria that they evaluate different offers against so that they don’t get caught up in the moment. For me, the three main reasons were the team, the role, and the problem space. 

From a team standpoint, after interacting with the founders I got the sense that they were really excited about working on an unsexy but meaningful problem. They thought about this space in a unique, consumer-first way which was unlike how most fintech data service companies operated. This forward-thinking vision they had made me think they were the right ones to tackle this problem. I also was excited by how sharp and personable they were, which made the prospect of working with them exciting. 

The second thing was the role. “A founding product manager role was really exciting but it can be sink or swim. I realized that the fact I was nervous for the opportunity was the reason I needed to take it - I knew it would be an incredible opportunity for growth (which ended up being the case). I was also excited to define and cultivate a product team culture and establish the norms for how Product operated.”

The last thing was the problem space. One way to evaluate startups is to look at the market risk, and with Truework there was already a large addressable market and high customer pain. 

How did you evaluate your startup offer? 

I ran three scenarios: a bearish, an expected, and a bullish case for where I thought Truework could end up, then tried to assess my equity in each of those cases. 

I also would factor in further dilution which is something people sometimes forget about. If someone joins and they are given say 20 basis points of equity, they sometimes forget that a valuation later on likely would need to account for dilution for the company to achieve that outcome. I made sure to factor that in, and then looked at each of these three scenarios and what the dollar amount would be in each of the scenarios. 

It was obviously high risk, high reward, but even in a mediocre startup outcome, it was far more appealing to me than working at a midsize or large tech company because I knew my personal growth would be a lot more and you can’t put a price on that. 

What was your original mandate at Truework?

I was hired to be the first product manager and take the reins of product ownership from the CEO. I was going to bring more process and structure to how Truework prioritized and planned what products to build (both on the quarterly level and on the sprint level). 

Soon after operationalizing the product function, I was given the mandate of owning the entire extent of Truework’s product. This included products for verifiers (which is someone who needs to verify someone’s income or employment), our HR and employer solutions in addition to a little bit of the consumer products that we had. Within 2-3 months I owned all of Truework’s product surface area. 

How did you build trust with the CEO to take over product so quickly?

One big part was deeply understanding where the CEO wanted to take the product both over the next 3-6 months and the next 3-5 years. I was aware of that context. Early on, the CEO and the CTO were both still involved in the day-to-day – they would sit in on planning meetings and chat with the engineering manager to make sure everything was going okay.

But as soon as they realized things were stable and that I was able to run things pretty independently, it opened them up to work on other priorities. I gave them leverage. 

What stood out about the early culture at Truework?

Two things come to mind. 

First, there was always a sense that we were all in it together and wanting to succeed. This was easier when it was a Series A company and we only had 20 or 25 people, but it’s been true later on as well. As companies get bigger, a lot of times people end up in silos and just end up caring about what they are specifically responsible for, but at Truework we’ve done a good job of having the team put the company’s success first. 

Second are the company values. We have four: be resilient, value diverse perspectives, put consumers first, and design the future. A lot of companies have values but don’t really live them everyday, but Truework consistently reiterates them in interview processes, hiring panels, all-hands, etc. 

My favorite core value is “be resilient”.  Startups aren’t easy. A lot of people at Truework have experienced low lows and they’ve had thick skin to get out of it. We embody that as a culture that even as the company scales people feel comfortable to take risks. I think it should be a core value for any startup. 

Who are a few people at Truework that inspired you in a unique way and what made them inspirational? 

Of course there were many exceptional folks that I worked with, but I’ll lower it down to two. 

First was Zach Ennenga who is a senior staff engineer at Truework. I’ve worked with many engineers in my career and Zach has a rare quality where he can zoom in multiple levels to get into the nitty gritty of a problem but also quickly zoom out to talk about the business and operate at a high level. 

He also embodies “strong beliefs, weakly held”. He doesn’t back down if there's a disagreement, but if evidence is provided to the contrary he’s very willing to change his mind. He would challenge me on ideas and force me to come up with a better approach to solve a problem or have a more refined argument. 

The other person was Felicia Lee who is a Director of Implementations. She pretty much became our chief problem solver and always adapted a company-first mentality. She doesn’t stick to established lines of ownership necessarily – she’ll figure out if there’s gray areas that don’t have accountability or have a negative effect on the customer experience, then she’ll step in and own it. She’ll get into the weeds and learn about a problem then establish a playbook to make it easy to manage or scale the solution. 

Doing the unsexy work that goes beyond your defined role isn’t something that’s talked about much at startups, but getting it done is admirable and really adds value to startups that are moving really fast. 

Were there any “holy crap this is actually going to work” moments? 

Initially Truework worked with a lot of small and medium sized lenders. We had a large number of small customers. Soon after rolling out an enterprise offering, one of the largest lenders in the country came inbound, asked to partner with us, then moved very quickly. This was probably three months into Covid where everyone was still figuring out how to even operate in a remote setting and here our revenue almost doubles overnight with just one customer. So that was the good part. 

But this customer had a pretty demanding set of requirements. Truework was forced to mature in a few weeks from a smaller business serving smaller customers to a business serving a really large enterprise. It was both thrilling and nerve-wracking to be a part of and that’s when I realized we were playing with the big boys now. 

Were you ever worried Truework was going to fail?

Truework has always had a stable product-led growth motion that provides a decent amount of top-line revenue growth. But I have been concerned (like a lot of people at startups) with how big the company could be. Will we have a massive impact or just kind of flatten out into mediocrity? 

The biggest moment of doubt for me came about 3-4 months after that large enterprise customer onboarded because that same customer churned from Truework. We had doubled revenue overnight, were really excited and had shared that with investors, but now we had to explain why our revenue graph had a steep downward slope. Emotions ran a little high. 

But what I was most happy about was how the team overcame that challenge. It was a big wakeup call for us to add more protections in our contracts to make sure Truework was viewed as a long term strategic partner for our customers (instead of a temporary overflow solution, which is what happened in this case). 

The takeaway here is that the lows can get really low and the highs can get really high but nothing is generally as bad as it seems. The process of building a company is iterative. A few big wins or losses don’t define a company. 

How did you manage your startup equity?

So I’m a firm believer in exercising early as long as you think the valuation isn’t highly unreasonable. 

If you join a Series A or Series B startup, the price of exercising is so low, because the strike price is so low, that you should just do it to save on the taxes. Once you get to Series C or D stage, you need to be more mindful of what the strike price is, where the market is and if you feel like the valuation is fair. For a lot of companies that raised in 2021 the valuations might be too high and we are starting to see some of them being marked down. If that’s the case, maybe wait a little bit and don’t early exercise because you may be negative on your options after. 

How did you educate yourself about startup equity? 

One thing I’m grateful for is that Truework offered employees early exercise. Not every company does it but it’s a really nice benefit for employees. While they didn’t teach me every detail about equity and taxes, they made me aware of my offer and the important timelines. It created a sense of urgency to quickly learn about this and take action. 

If you don’t know about equity yet, think about it this way: what’s the higher ROI, spending an hour or two to learn about tax implications of your decision, or spending it on your day job? It’s far higher to learn about your equity. In your job offer you might have the option to negotiate a higher cash salary or higher equity, and having the right information can be worth five or six figures later on. 

It’s your prerogative as an employee joining a startup to understand this. The company can make it easier for you by providing training materials (or you can look at Compound’s Manual), but at the end of the day it’s on you to understand it.