MarTech Interview with Rikin Diwan, SVP of Marketing at Thimble

A big part of scaling marketing ROI involves first establishing long-term customer relationships that drive repurchase and retention opportunities, Rikin Diwan, SVP of Marketing at Thimble shares more:


Welcome to this MarTech Series chat Rikin, tell us more about Thimble? We’d love to hear more about your role there.

Thimble provides insurance for small businesses with big goals. The commercial insurance market is massive, more than $150B in annual revenue in the US alone, but it hasn’t evolved in decades. Thimble has a very unique offering that’s made quite the dent in the industry since launching in October of 2019. 

Simply put, Thimble disrupts the industry’s approach to time and technology. Instead of an annual contract, small businesses can get coverage by the month or even by the job (down to an hour). And, instead of finding an insurance agent and discussing options or making changes over the phone, they can get instant coverage from the Thimble app or from

As SVP of Marketing, I oversee Growth, Brand, and PR & Comms. I met the team during a hectic rebrand process in August 2019, just two months before the slated launch date for Thimble. During the interview process, I remember gushing over the business model, but being outwardly critical of a work-in-progress logo that the agency was pushing. Oddly enough, I think my honesty got me the job, but then of course we only had 4 weeks to get things right! Luckily, we all love the logo they came up with.

Since those early days with Thimble, we’ve been heavily focused on growth. What’s great is that while we’re a B2B solution, our distribution strategy looks a lot like a D2C e-commerce company. Our main channels are search, social, affiliates, and partnerships – and we’re busy scaling all of them today.

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How are you seeing marketing teams and role change in today’s marketplace? According to you, what are some of the top skills needed in marketers of today?

In my opinion, marketing has become the most multi-disciplinary team within the org. For a long time, the equation was that marketing equaled the combination of branding and advertising. However, in today’s marketing team you’ll find analysts, developers, and product managers sitting alongside sophisticated channel/partner managers, strategists, product marketers, creatives, editors, community managers, and more. 

This expanded scope is great because it truly brings marketing to the table for key business decisions. However, it also means that the role of any individual marketer, especially a leader, is more challenging than ever before. We can no longer simply think and communicate our efforts in clicks, impressions, or even awareness. Marketers today, regardless of their role, have an understanding of the economics of the business and think in terms of CAC, LTV, payback periods, and ROAS. 

The best marketers, whether a growth marketer or art director, are able to provide clarity back to the business.

What are some top B2B marketing trends and B2C trends that you feel are now becoming more center stage in the marketplace?

I recently wrapped up an 8-month search for a Head of Growth for Thimble and, although gruelling, it was a great opportunity to peek behind the scenes and into the minds of dozens of B2B marketers and a few B2C ones as well. What was clear and exciting to see is that every company was focused on their e-commerce offering. 

E-commerce is a boon for our discipline and entire industries are shifting in its direction. Within B2B, lighter weight product offerings are being created to move down-market so-to-speak. The B2B marketers I spoke with were discussing “assisted” vs “unassisted” sales. “Unassisted” require new products that are easy to understand, well priced, and simple to transact without the need for sales teams and long sales cycles. I don’t think there is a shift away from Sales to Marketing necessarily, but just an emergence of Marketing as a parallel growth driver of a business. 

At Thimble, we’ve started with this consumer-first B2B offering. Our insurance products are positioned directly at small-business owners and often the sole decision-maker in the types of businesses we cover. We’ve changed both the format of insurance but also the distribution of it as well – we are literally the only app in the AppStore where a handyman, landscaper, photographer, etc. can buy business insurance instantly. I often say that we are so D2C in our approach that we are the first lowercase b2b company. 

B2C has a head start but it’s clear we’re in the early days of e-commerce everything – just look at the leaps and bounds made under the pressures of the quarantine. For marketers, what is exciting across both business types, B2C and B2B, is the convergence of strategies such as subscription products and skills such as lifecycle marketing. It’s a great time to be a marketer. 

Take us through the kind of marketing technologies you have often relied on in the past to drive marketing ROI?

I’ll highlight some of my favorite tools because covering them all would take a long time. 

First of all, I wouldn’t be able to run the team without Asana and Looker.

All projects are in Asana, all planning is done in Asana, and even my own to-do list is kept in Asana. It’s not a perfect tool but it’s the best tool I’ve come across and I find it necessary to be militant about the use of Asana across my team so that we can keep track of all the projects and workstreams we have going.

From a data perspective, you need a business intelligence tool, and if set up properly it helps us translate marketing metrics into business terms which I mentioned previously. At Thimble, we use Looker and I think it’s the most intuitive BI tool I’ve used to date – and have loaded it up with custom dashboards. Every Monday, I present a unified dash of performance to my co-founders and fellow leadership team.  

Beyond those two there’s a longtail of tools we use to run the business. 

My team is obsessed with experimentation and even our designers are love the tangibility of progress provided by tools like Google Optimize, Optimizely, Amplitude, Fullstory, and some of the built-in testing features of our CRM (Iterable).

I open SEMRush every morning, spend time in Google Ads and Search Console, and am increasingly digging into Facebook, Impact Radius, and other platforms. Our social agency has a proprietary tool to experiment with Social creative that blows my mind each time we review campaign performance.  

And finally, as a fully remote company, we collaborate over Slack and Zoom, which is challenging for brainstorming but can unlock productivity if used wisely. 

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As the need for deeper intelligence and insights grows, how do you feel marketing leaders can optimize how they enrich their data and business intelligence to drive strategies?

Survey data is a big part of our marketing strategy at Thimble. We frequently launch surveys and questionnaires to collect voluntary information from our customers about how they’re feeling about a number of things related to insurance. We recently launched a project called The Comeback. It was a report we compiled using responses from 50,000+ SMBs to assess the state of business right now. The goal was to equip our customers with valuable insights that they can use to make decisions about their business in the post-pandemic era that we’re entering.

It’s extremely valuable to have access to this type of data from the audiences you’re serving because it allows you to fine-tune your strategies and ensure you’re effectively creating distinct value for customers. It’s why I think taking similar types of pulse surveys, especially as your audience grows, should be a regularly implemented practice. 

A few last thoughts and takeaways for marketing leaders and CEOs/CMOs to keep in mind through 2021?

My biggest takeaway is to keep your audience the core of what you do. For Thimble, our audience is small business owners, and this has been a tough year for them to say the least. Knowing this, we’ve done everything we can to ensure we’re consistently listening to their needs and ensuring our products are making their lives easier, whether they be established SMBs or first-time entrepreneurs. If you’re able to laser in on specifically who you’re talking to and what their needs are, you’re able to fine-tune your marketing strategies to create loyal, lifelong customers.

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Thimble’s mission is to make insurance simple, to help businesses succeed on their own terms. Available by-the-month or by the job, Thimble coverage takes less than one minute to obtain and can be modified, canceled, or paused at any time. Thimble has sold over $175B in coverage since its inception.

Founded by Jay Bregman and Eugene Hertz, Thimble is based in New York City and has raised over $45 million in funding from IAC, Open Ocean and other top firms. 

Rikin Diwan is the SVP of Marketing at Thimble


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