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It’s All in the Details: A CFO’s Perspective on Raising a Series A

Raising a Series A is hard, but detailed prep work and close team alignment can keep you in control of the process. Here's my deep dive into how we ran our streamlined Series A fundraising process at Rewind.
Alamin Mollick, Head of Finance at Rewind

From kickoff to close, Rewind’s $15m Series A raise took 11 weeks, and we spent about three weeks preparing for the raise. At first glance, this might look like a fairly straightforward timeline, but a lot of detailed preparation went into planning the raise and determining what it would look like. This up-front work kept things running smoothly throughout the 11 weeks: it helped us stick to our schedule, anticipate investor questions, and keep everything polished and organized.

My role as Head of Finance during our raise

The role I played during our raise was complementary to, but different from, the role of our CEO. One of my most important tasks was to build a compelling financial narrative based on the company’s metrics over time. This also involved drawing careful comparisons to peers about the benchmarks we had met. I also had to speak in detail about the “use of funds”–how we planned to use any capital raised to hit the next set of milestones. CFOs tend to have pointed views about how target operating metrics will be hit, what the splits between the different levels of headcount are, and the guiding ratios that will drive planning.

In addition to this financial storytelling, I also worked behind the scenes to backchannel references on investors by talking to their portfolio companies. During a raise, CEOs have to focus on taking lots of investor meetings and building relationships. They’re so busy being the public face of the company that they may not have time to chat with other founders and CEOs to get honest feedback on the investors they’re pitching. Investors provide a set of references, of course, but it’s always a good idea to do your own due diligence. This is where I came in: I met with portfolio companies to get unfiltered opinions while our CEO focused on building the relationships.

Nailing our pre-raise alignment

Before we decided to raise our Series A, my CEO and I made sure we were perfectly aligned on our motivations. We both strongly believed that the company had a unique market opportunity and was capable of being a genuine venture-backed profile–previously, we had focused on bootstrapping and received very little institutional funding. This was validated further when we chatted with Matt Roberts and Christian Grunt at ScaleUP Ventures (our first seed round investor) and also Alexandra Sukin at Bessemer Venture Partners (who we brought in a small seed extension round a few weeks before the Series A kickoff). We saw momentum in the numbers and knew that the numbers weren’t capping out, either, so we saw an opportunity to accelerate our growth. This meant that we wouldn’t be raising capital simply for the sake of raising capital: as the number one player in our market, we realized we had a real opportunity to get ahead.

So, he and I aligned on what the market was, the products, the unit economics, and the overarching strategy of what we wanted to do and in what time frame. We also wanted to align on the key documents we’d need to provide to investors along the way. We knew we’d need to show a lot more documents than we had in the past. For our pre-seed round, all we showed was a profit and loss statement, a three-year forecast, and a pitch deck. For our seed round, we needed more: our deck, financial projections, a product demo, our tech stack, case studies, our org chart, and a list of customers to contact. Our Series A round required some more financially-focused documents alongside other data. We needed a one-page teaser for external outreach, our pitch deck, cap table, some historical financials, a financial and operating model with detailed drivers, a cohort analysis, and raw data that investors could examine for themselves. Giving potential investors access to raw data actually helped us control the narrative: we had already worked with the data, reached conclusions we were confident in, and knew there were no surprises.

Month zero: Evaluating our fundraising readiness

This pre-raise alignment period was month zero of our raise. We wanted to figure out what the timeline and process would look like, align on an overall vision, and build a financial model that would tell us how far we could take potential investment capital.

During all this prep work, we realized we’d need to run our raise methodically, so we could control as much of the process as possible. The first four weeks would be nothing but business development, introductions, outreach, and sharing the first level of our DocSend fundraising data room which contained the one-page teaser and some basic financials. We also set up a HubSpot CRM for investor relations where we stored our target leads with information about when we had contacted them, the stage they normally invested in, and the tier in which we ranked them.

These are some of the questions we asked ourselves during our fundraising preparation.

Fundraising Readiness Checklist

  • Why are we raising?
  • Who’s within our first-degree network?
  • Do we have a list of questions to assess for investor fit?
  • Do we have a one-pager to send?
  • Are we ready for meeting #1, with an up-to-date pitch deck?
  • Do we have a tightly-knit story of how we got here? Where are we headed? Do our metrics and financial model line up with our story?
  • Do we have an efficient month-end closing cycle with minimal error to ensure investors get updated numbers promptly?
  • Can the team operate with us being 70% less available?
  • Are we due diligence-ready? Is our data room set up and easy to follow?

Month one: Leveraging our networks and anticipating investor questions

During our four weeks of business development in month one, I dove deep into my network. On the one hand, I checked in with fellow CFOs to get their thoughts on our approach. It’s common for finance leaders to share notes and numbers with each other; this way, you can be sure that you’re not telling stories about your business that aren’t necessarily true. On the other hand, I worked continuously in LinkedIn, HubSpot, and Notion to determine if I knew anyone at our target firms’ portfolio companies who could make an introduction.

Our Stack of Fundraising Tools

  • Calendly, Google Calendar for scheduling
  • Zoom for virtual meetings
  • Notion for managing funnel, meeting notes
  • DocSend for data room and due diligence
  • HubSpot for tracking emails
  • LinkedIn for finding key contacts and building out network
  • Pitchbook / Crunchbase / Investor websites to research portfolios and teams
  • Hunter.io for looking up emails

We started month one with a funnel of 54 different firms, and over those four weeks we narrowed things down and had second meetings with the firms we liked best. We decided that in week six we’d start accepting term sheets. We were able to stick to this timeline because we had done so much prep work and aligned so closely on the numbers and overall story: we ended up with an FAQ-type document that was around 20 pages long with answers to questions about things like CAC payback or gross margin. This meant that when firms requested second meetings with us after week two or three, we were ready with answers to all their diligence questions. We were also able to re-use these diligence answers since many of the questions we got were very similar. Being able to anticipate and quickly respond to questions really streamlined investor conversations.

Our criteria for evaluating investors

We also built a questionnaire for potential investors with our own scoring criteria. This helped us evaluate investors in a number of key areas: go-to-market expertise, SaaS expertise, corporate development/M&A expertise, follow-on financing capabilities, talent acquisition and headhunting prowess, leadership mentoring, and partnership networks. We ranked these categories by order of importance and gave firms scores as we learned more about them. Despite this list of criteria, the dealbreaker for us was if the CEO and partner at a firm didn’t have a good relationship. Without this relationship in place, nothing else mattered for us.

While we used second and third investor meetings to ask lots of questions that helped us narrow down our list of firms, we also spoke to fellow CFOs and CEOs at investors’ portfolio companies. These people were happy to share their experiences and opinions candidly because we were careful about establishing meaningful relationships with people in our network. I was also able to gain fellow CFOs’ trust as one finance person to another.

These candid conversations helped us create an offensive Series A strategy rather than a defensive one. Since we had so much information about the Series A marketplace, we were able to make firmer asks about our valuation and market multiple–we never felt lost when speaking to investors about these questions.

Month two: Narrowing our investor pool and getting to the term sheet

In month two, we began giving investors who were moving through our funnel access to another level of our data room. The second level of our data room contained our entire financial model, our cohort model, our raw billing data, all of our SaaS metrics, a product roadmap and product demo recording, and go-to-market data. From our initial pool of 54 investors, about 20 made it to this next stage, our goal being to narrow the pool down to about five by the end of the raise.

Our data room became a powerful intelligence tool that helped us prioritize conversations with investors. We got great feedback on our data room’s layout and organization–this was especially rewarding since we had hoped our attention to detail would help us stand out and show off our professionalism.

Our attention to detail paid off in other aspects of the raise, as well. We made sure to respond quickly to any questions about our data or documents. Our turnaround time and thorough explanations impressed investors and more than made up for any minor hiccups in our data. Being able to answer questions in a matter of hours got our investors closer to “yes.”

When answering questions, I tried to put myself in the investor’s shoes: how could I help them write a memo so that they’d explain our customer, product, market, go-to-market engine, and unit economics in the best way possible?

Month two is when we started seeing term sheets and began discussing things like board makeup and what the initial due diligence would look like. At the same time, we were doing our own due diligence on interested investors. We ultimately wanted to find a lead investor, so we thought hard about narrowing down our pool of investors to the ones we were most serious about: who could we imagine ourselves in board meetings with as a partner? Who shared our company’s values most strongly?

When answering investor’s fundraising questions, I tried to put myself in their shoes: how could I help them write a memo to their partners that explained our product, market, customer, go-to-market engine, and unit economics in the best light possible? Click To Tweet

Choosing our lead while leaving room for strategic investors

In the end, it was easy to decide on Inovia as our lead investor. We had great conversations with Magaly Charbonneau (Partner) and Alex Barrett (Associate). They moved through the process so quickly: they went deep into the data room, met our executive team right away, and quickly arranged a meeting with their entire partnership team. In fact, they had such high conviction in us that they turned around the term sheet in just ten days from our introductory meeting.

We also wanted to bring on other institutional investors alongside Inovia. By gradually narrowing the pool, we hoped to select a small handful of firms to complement our lead. We were incredibly excited to partner with Ridge Ventures, meeting with Yousuf Khan and Brendan Baker, who would be able to help from a networking and strategic partnerships perspective. We were already thinking ahead to our next level of growth and wanted to partner with firms who could help us get there.

In addition to these institutional investors, it was crucial for us to leave room for individual strategic investors. These were people like the former Head of Technology Investment Banking at JPMorgan, the former Head of Strategy at Microsoft, the CFO of GitHub, or the former Head of Corporate Development at Zendesk. Our strategy was to include in our cap table a number of people who could help us down the road on matters that didn’t necessarily involve money. Founders at the Series A stage should think about making space for individual investors: these are people who add credibility to your company and can serve as sounding boards. I’d recommend that founders leave up to 5% of their rounds open for strategic individuals.

I recommend that founders leave up to 5% of their rounds open for strategic individuals. Our strategy was to leave room on the cap table for those who could help us and add value down the road on matters that didn’t necessarily involve money. Click To Tweet

Month three: finalizing the close with the help of our data room

Once we pinned down the investors we were going with, month three was all about finalizing the round. This involved background checks from investors as well as some adjustments on our end: for example, we had to update our employment agreements and make minor changes to our employee stock option plan.

We created a separate, second data room just for diligence that we shared with all the lawyers and our lead investors. This data room contained documents like monthly board meeting notes, our product roadmap, and legal materials that had been requested. Having a second data room was especially convenient: everyone knew where all the documents were, could see when new files were added, and could stay aligned in a centralized space with only one link. As with our fundraising data room, it helped that we put a lot of thought into our diligence data room’s structure and organization.

Alamin Mollick of Rewind's virtual data room example in DocSend

Do the simple things well and stay realistic

Staying so organized throughout the raise has given me clarity on some simple things other Series A founders can learn from our experience. First, remember that professionalism counts for a lot! Get back to investors quickly whenever they write you–they’ll note your responsiveness and it will certainly work in your favor. Second, when sharing your company’s story or metrics with investors, put yourself in their shoes: work as if you’re helping them write a glowing investment memo about your company.

Next, make sure to level up your data room game. The quality of our virtual data room helped us gain significant credibility with potential investors. We constantly received feedback that it was one of the best, if not the best, that investors had ever seen for a Series A raise. Finally, when it comes to sharing financial models and projections, it’s better to stick with one realistic story or model rather than presenting multiple scenarios. Having conservative and optimistic models that dramatically shift the story will only lead to more questioning and skepticism–don’t give investors a chance to count you out.


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