Interview with Trevor Sookraj, growth marketer turned founder

Trevor Sookraj is a growth marketer turned founder, currently running Divisional — a managed marketplace to help startups connect with growth talent. Since 2021, he has helped 50+ startups work with growth marketers, including Openlayer, Verifiable, and Paragon.

This interview is part of a series by Compound. Compound provides everything you need to manage your personal finances (advice, tracking, investments, taxes, borrowing, estate, and more).

How would you describe the role of marketing at a startup? What do you believe are the attributes of a great marketer?

Both ‘marketing’ and ‘startup’ are wide-reaching terms, so I’ll focus on ‘growth marketing’ and ‘early stage startups’, as that’s what I know best.

Growth marketers help startups find scalable ways to drive revenue. This separates them from sales reps, as while they are often involved with outbound sales, pricing, and other activities, their goal is to build repeatable processes for the startup. An Enterprise BDR can pound the phones and personalized emails, working 80-hour weeks to generate 5 demos. A growth marketer might use a combination of data (shout out to Clearbit), software (i.e. Woodpecker, Expandi), and advertising (i.e. LinkedIn account lists) to meet the same goal. The difference is that the growth marketer’s practice can be repeated with less effort in the future.

In practice, this often comes down to running experiments to test what startups & founders think they know about their target customer. What pain points do they have? Which are the most acute? How do you create messaging that presents your product as a solution? Combine these essentials (product marketing) with getting in front of your target audience (demand generation) and you get the modern growth marketer.

On attributes; the most important attribute I’ve noticed across the 70+ growth marketers that I’ve hired is empathy. 80% of the experiments you run will FAIL, and it’s very easy to get demoralized. Marketers who don’t understand how this lack of progress impacts the founders and the startup will never be successful, because they won’t take ownership of making it a success. A former employee of ours, Brian, spent 6 weeks with a Dev Tools startup (Paragon) running campaigns that didn’t work. He kept learning and iterating, which Paragon’s CEO (Brandon) appreciated. Once things started to work, Brandon knew he needed Brian on full-time. They’ve since raised a $16M Series A.

The other two attributes that come to mind are often at odds with themselves: systems thinkers and scrappy. The latter is something that all startups love; someone who isn’t afraid to get their hands dirty to launch campaigns and dig deep if they don’t work. I’ve built full teams (Head of Growth, Growth Marketing Manager, Designer, etc.) but projects stall at 80% if the Head of Growth isn’t willing to (or able to) launch campaigns themselves. This can be contradictory to the former… Oftentimes, ‘scrappy’ means ‘doing it yourself’, which is a recipe for burnout (and not a great marketing hire). When campaigns work (and they eventually will), the first question the marketer should be asking is “how do I get this off my plate + scale it?”. One of our Heads of Growth, Gagan, worked with Openlayer to create email copy, determine the ideal prospects, and launch the campaigns. However, once the engine started to hum, his immediate reaction was to bring on a BDR to handle responses, stay on top of cold leads, and book qualified demos for the founders. This allowed them to scale to 30-35 qualified demos per month and take the function in-house, whereas a marketer who just executed would have made this their full-time job (instead of leaning on a BDR).

How did you “break into” marketing? What was your first marketing job?

I started out in tech sales because I wanted to get compensated for the results I drove for a company. However, I knew I wanted to eventually be an entrepreneur, and sales had less ‘hard’ skills than I was looking for. I started to read up on marketing — blogs like that of HubSpot and Close.io, and created my first wedge around “CRM marketing”.

I then wanted to put these ideas to practice - how would this work at an actual startup? I reached out to a few Toronto tech folks, namely Bennett Fitzgibbon (Turnstyle Solutions, acquired by Yelp) and Richard Wong (#paid) to share what I thought I knew about marketing and ideas on how I could help. Turnstyle was my first gig, even though it was part-time as a Marketing Intern. I helped them with organizing their CRM for lead nurturing and creating new landing pages for specific personas.

It was at this point that I caught the marketing ‘bug’ and wanted to double-down. While I stayed at Shopify Plus and transitioned into Revenue Operations, I continued working with other companies on the side to broaden my ‘Marketing T’ (link to Buffer article) and cover data analytics / SQL and go deeper into email marketing (both inbound automation and outbound sales).

You joined Clearbit fairly early on—what was the pitch on why you joined?

A lot of people talk about unconventional ways to land a job, and Clearbit was exactly that for me! I was working at Shopify Plus and my friend Steeve saw a Tweet from Alex MacCaw, the CEO of Clearbit, looking for a hire who loved sales but also knew SQL (link to the Tweet / image). He encouraged me to shoot Alex a DM and see if I’d be a fit — worst case, it’d be a good conversation, right? Over the next 3 weeks, I went through interviews with Alex and the sales team … The further I went, the more I thought this could actually be a reality. Keep in mind that Clearbit was a hot San Francisco startup, and as a Canadian in tech, working at an SF company was the mecca.

So, I did everything I could to stand out — I made a deck with my past experience in sales + SQL, taking (info redacted) screenshots of dashboards I had made. I wrote them outbound email sequences based on the persona they were targeting, and even recorded voicemails that I’d leave for a potential prospect.

At the end, Alex decided I wasn’t the best fit for sales but I had a great head for growth, and invited me to join Matt - co-founder and then Head of Growth at Clearbit - on his team. A couple weeks later, I emerged from 16th St Mission station with two suitcases and a Craigslist room, ready to work!

Why I joined — the simple pitch was that Clearbit had all the makings of a startup unicorn. Not just in terms of product / TAM, but that was impressive too (keep in mind that data enrichment, lead scoring, and prospecting was not as pervasive today as it was in 2017). Instead, it was the team that got me excited… Alex was an early engineer at Twitter + Stripe, and had a rockstar team (then, 22 people) from Heroku, Dropbox Business, Google, Opendoor, and so many others. I knew I’d have a great opportunity to make an impact at Clearbit, but the community I’d build would be infinitely more valuable. My colleagues (and good friends) have gone on to become clients, mentors, and much more.

What was the marketing team like when you joined? How big was it and who did you work with?

Despite not being a traditional ‘unicorn’ at the time, Clearbit was very unconventional with their startup trajectory. The companies I had work for in the past were VC-backed and on a treadmill; get results, find repeatability, raise your next round, and keep going. Clearbit was different… They had multiple $M in ARR, raised a Seed but were profitable, and had a ton of business models going — self-serve (a 7-figure ARR line of business), B2B sales, partnerships (both Salesforce / Data.com and other players like Intercom, Drift, Base CRM, etc.), and much more. In contrast, the ‘business’ team was 1 Head of Growth, 1 Chief Business Officer, and 2 sales reps. Talk about efficiency!

What that meant is that there was a LOT to do. The team was initially myself and Matt, with Nick Wentz joining a couple weeks later to lead up the Clearbit Connect wing (Gmail + Salesforce extension) and provide a more experienced set of hands for Matt. While Clearbit was making a hard push on B2B sales, they had a thriving self-serve business (developers, SMBs, etc.) that was underoptimized. This was my responsibility, in addition to helping Matt/Nick with the other marketing campaigns.

The most unique part about Clearbit’s marketing team was the emphasis on experimentation. Every idea we had was organized into an Airtable spreadsheet, given a score (ICE - Impact, Confidence, Ease), and prioritized during a Sprint standup we had every 2 weeks. The experiments had clear expectations — what was success, failure, when did we keep going VS call it quits. What this led to was a rigor around being ‘data-driven’ that I had never seen before: I’d have an idea for a campaign, and Matt would show me an entry from ~ 3 months ago of what he did and why it didn’t work. We never made the same mistake twice.

A couple of months later, Brian joined the team as a Growth Engineer and that really opened up our opportunities — we could build calculators and free versions of our product as lead magnets, and I worked with him on a lot of the reporting pieces (i.e. using Mode Analytics to build a dashboard to show marketing-influenced revenue).

Overall, the marketing team functioned where each member owned a specific LoB and/or area, and was responsible for completing their experiment(s) by collaborating with other marketers. I worked with both Nick and Matt on several projects, especially when it came to feature launches or company-wide initiatives, but had ownership of self-serve.

How did the marketing team set priorities? How did you communicate those priorities across the company and how did you hold yourselves accountable to them?

The experiment pipeline was the primary way that we set priorities. Matt was involved in leadership meetings and would communicate those priorities to us, i.e. quarterly / annual goals and what that meant for marketing. This would affect the ICE score of our experiments, as impact would differ based on the over-arching KPIs that our team was shooting for.

Sharing those priorities across the company was a bit more nuanced - sometimes it involved attending the meetings of other teams (i.e. sales) to communicate what we’re working on and getting their input. Often, I would create an overview and meet with the head of a department (i.e. Customer Success) to share how it would impact them, and to get it on their priority list. A lot of marketing initiatives are not siloed, so it’s important to get buy-in — if sales isn’t interested in a new lead source, they won’t work them over other opportunities (even if they’re qualified). I also used my lead, Matt, as a shield for incoming requests - he would push back if my time was better spent on other activities, and that prevented being overloaded with tasks.

Accountability differed based on the level that we’re talking about — since we each owned an LoB, Matt would have a conversation with us if stats weren’t improving and we weren’t making progress. This was typically data-driven, as we could point to specific experiments that failed, and see what the root cause was. The over-arching company prioritization was less structure — there were weeks / months that were more intense based on the need to hit ARR goals, and there would be pushback (i.e. budgets cut) if we didn’t hit those goals.

What was Clearbit’s culture like? Were there any particular cultural rituals that were memorable?

Clearbit was a work hard, play hard environment, with an emphasis on avoiding chaos. This is such an important point, as my impression of Silicion Valley startups was the opposite of what I expected when I joined. Few people worked well into the night, and Alex (CEO) was one of the few who came in on weekends. I asked Matt about this, and he shared that the co-founders had all worked at ‘chaotic’ companies, and saw how toxic it was for growth. For that reason, Clearbit was a meritocracy - get your work done and do it right. I still put in extra hours to ship a dashboard or work on new projects, but it felt more because I was passionate about it, and not because I had to.

One culture ritual that I LOVED was the memos that Alex sent out to the entire company about the early days at Clearbit. He talked about their journey to $100k ARR, how he thought about new products, and much more. I reflected on this after working with many other startups, and think that it’s an invaluable practice. Employees can’t always see what co-founders are thinking, and more importantly, they don’t know what happened to lead them to think that way. The more clarity we got into how Alex thought and functioned, the easier it was to come up with new ideas that aligned with his vision and what Clearbit was striving to be.

On top of that, Clearbit had all the typical in-person culture that I loved + now miss — playing in a kickball league, grabbing lunch at Kitava with other employees, doing a bar crawl for Pride Week — these were all ways to humanize the people I worked with and made it feel like this was more than just a job. While I don’t think it works for every organization, this made Clearbit my most memorable work experience and created friends for life.

You eventually started your own marketing agency. What was that experience like? How did you get your very first customer?

I never thought that I’d start a services business — venture-backed tech was the only world I had ever known. But when I joined Dorm Room Fund in 2019 and met someone who was running an agency, it was very intriguing to be. Post Clearbit, I wanted to get the most exposure to startups to test what I had learned, and see what area I was most interested in.

That individual (Harris) was actually how I got my first client. I teamed up with another DRFer (Phillip) and created an agency, to take on a client that Harris didn’t have capacity for. With outreach to our network and referrals, that eventually grew into a roster of clients, and moved from hourly engagements + project-based work, into monthly retainers and a team that we could contract the work to.

The experience was eye-opening because it showed me how most businesses in America function: bootstrapped and based on profit/loss. This was the first time I had full autonomy over a company, and saw the impact that each of my decisions had. I think the biggest step for most founders is deciding on a price point, and it’s an exciting experience to have someone pay you for a good / service. It’s even more exciting when you charge the next person 25% more and do it again. I think that’s the joy of business building; seeing something go from an idea and an individual to a full organization with repeatability. Over the past 2-3 years, that evolved into Divisional, where we have a small full-time team of ops/recruiting and a network for 80+ marketers.

What is day to day like running your own agency? You wake up—how do you spend your time throughout the day? How do you decide how to spend your time?

This was an iterative process for me; in the early days, I treated every day with a long task list that I worked through. That was because we didn’t have any employees, so all the work that happened was a direct result of my effort.

That evolved into my current setup, where I can’t be the individual contributor to push projects forward. I think that’s a huge realization for most founders; while you can technically do all the work, it’s inefficient and prevents you from being able to think long term.

I’ve recently started using the Getting Things Done framework, and adding more rituals and processes to stick to that. I start my day by reviewing my Things inbox, identifying the top 1-3 priorities, and doing a few rituals (triaging HubSpot tasks, responding to sales emails, updating ClickUp tasks), before getting into the day. I try to block at least 1.5-2 hours of ‘deep work’ every day, where I can work on tasks that require more critical thinking.

My time split varies — some days are packed with sales conversations and interviewing new marketers, while others are relatively open where I’m working on SOWs for new clients or talking to my internal team to get aligned. I try to have my days reflect the OKR system that some companies follow - the priorities for the day (time spent) are based on the weekly priorities, which ladder up to the month, etc. My biggest challenge is not getting sucked into firefighting or short-term activities, and constantly seeing what I can delegate to my team and course correct, instead of just ‘doing’.

Personally, I know there are a few things I have to do to be successful in the week, and I always carve time for them. That includes exercising every 1-2 days (typically after work) and getting social time with friends. If I’m feeling low energy or off, I can go to that checklist to eliminate some of the most common factors (and 90% of the time, it’s usually one of those).

What do you think separates a good marketer from a great marketer?

I believe that marketers have two skill sets: their ability to think and their ability to do. Every founder will optimize for different things when they hire; I’ve seen founders optimized for ‘thinkers’ if they come from ops / consulting / banking backgrounds, as they’re looking for someone who can build a strategy and hit goals, but not necessarily execute on it (use freelancers or agencies). Likewise, I know founders who have a high degree of conviction around their ideas, and want a marketer who can ‘do’ all the activities (i.e. launch campaigns across different channels) but not necessarily challenge the overarching narrative.

For me, I think that the latter (hard skills) is table stakes. I don’t think it’s hard to learn how to do email marketing well, Google Ads, etc. Good marketers might be better at this than the average Joe — they can optimize an ad account that’s underperforming, launch a bunch of campaigns that the founders had on the todo list, etc.

Great marketers have both the hard skills and the ‘thinking’ part down. They always look to first principles and how the customer reacts, which rubs some founders the wrong way. If one marketer wants to talk to 10 customers in the first week and instead you choose another marketer who wants to execute on your laundry list of campaigns, you’re likely hiring a good marketer instead of a great marketer. Great marketers need a proper foundation to think from, and that involves talking to customers and constantly challenging the assumptions of the founders. This of course changes when you hit the later stages and have Product Market Fit, but early stage marketers need to embrace this, just as much as the founders do.

I’d also challenge the notion that great marketers are ‘data-driven’ — all marketers should be data driven, the question instead is are they data literate? Just because a marketer can run a SQL query and get answers on product analytics, or create a dashboard for Google Ads doesn’t mean they’ll make the right decisions. A great marketer knows what questions to ask and how to interpret data, even if they can’t always pull it themselves.

Do you have any favorite marketers? Companies you particularly admire that do marketing really well?

1. I’m a big fan of Guillaume Cabane, former VP Growth at Segment, Drift, and Gorgias. His perspective on experimentation was one I followed closely at Clearbit, and he frequently collaborated with us on articles on how to run data-driven campaigns.
2. For non-marketers (who are great for marketing), Parthi from Letterdrop has been great to follow. He’s a big fan of social selling, where you engage with your prospects on LinkedIn and use those narratives to push your brand forward. Adrian from Verbatim Studio is also great for this!
3. On the company front… I would go with Omniscient Digital. Their Founder, Alex Birkett, started out at CXL and is a value-first marketer, which I think is so rare nowadays. Through Omniscient, they don’t just talk about thought leadership, but actually write articles like this one with practical advice and free guides.
4. I’m also a huge fan of companies that create content / demand engines, using their product. APIsec is a great example of this, where they have a free scan and a course on API testing. This goes so much further than simple content, and actually makes you the go-to resource + value-add in your field.

This interview is part of a series by Compound. Compound provides everything you need to manage your personal finances (advice, tracking, investments, taxes, borrowing, estate, and more).