Hannah Jarrett's Artifacts
Moments of impact from Hannah Jarrett's career
DealRoom · VP of Marketing
The Pain Campaign: 50 Halloween Mailers Drove 5 Deals & What I Changed the Second Time
Around Halloween last year we launched what we called the “pain campaign”. It was all about driving awareness (surfacing the pain) of the spreadsheet nightmare that is running M&A in excel. Q4 is huge in this market. Firms are planning for next year, they're often getting a new fund, and that fund comes with a mandate like "acquire three companies per quarter" when they did three all year. It was the perfect time to leverage awareness tactics both at an ABM level (targeted accounts) AND the general M&A space. What we sent For targeted ABM, we sent custom mailers with messaging designed to surface the pain of manual M&A . There was a squishy coffin stress ball, a Starbucks gift card stamped with “ wake up from the spreadsheet nightmare”, a rock ice maker stamped "here's to the deal," wrapped in a custom sticker that said "because on the rocks should describe drinks, not your deals”." Everything was wrapped in spiderweb paper with other Halloween touches. I tried to lean useful, not kitschy. Then my team (who are the best) took the mailers to that creepy old cemetery by Park Street in downtown Boston and shot photos of them there. We used those photos on social to build buzz around the pain campaign and "death to spreadsheets." We sent about 50 mailers and had 10% conversion to hand raisers: 5 deals. What I'd do differently Because we were bootstrapped, I did it all myself. I found each individual item, worked with our designer on a custom on-brand sticker for each one, and hand-packed every box. It wasn't a joint effort with sales the way it needed to be. So over the summer we simplified. Our ICP is predominantly men in finance, so we did golf kits: Dealroom golf balls, tees, and a golf gift card people could use at different courses, in a pouch with a bit of swag. Everything was pre-made except one custom piece. For non-golfers, one of our sales reps came up with mini L.L.Bean totes. The bigger change was who picked the list. Instead of me choosing, reps flagged an outbound account they felt needed awareness. I'd pack the kit, and they'd run it to UPS themselves. Those kits performed even better, because they usually went to someone a rep was actively trying to reach. That became what we called ABR, account-based revenue. I think ABM is destined to fail if it's just on marketing. With ABR we niched down by industry, built landing pages with specific case studies and snippets, and ran it in partnership with the BDR team. Way more effective than "here's a list, we'll send gifts, you sell if they call." Built with: Becky Chariton, Associate Director of Brand & Buzz Amber Green, Senior Brand & Content Specialist Macy Wilcox, Customer Marketing Specialist
Validated by 1MWWhy I Moved Dealroom Off 90% Inbound: Diversifying Pipeline Sources While Growing SQLs 138%
When I came in, Dealroom had no outbound. I'd estimate that about 90% of closed-won deals were inbound, plus a referral motion. Inbound is fantastic, but we knew we couldn't survive on it forever, and that was a big part of why I was hired. We were already creating a lot of content. We have a founder-led podcast with real practitioners talking about M&A. We then take the podcast content and squeeze all the juice out of it: an infographic, four episodes combined into a white paper, and templates for how to run deals, which people which are highly downloaded. The problem was that those downloads were just sitting there. Nobody was asking what happened next. What we saw was that people would download, engage, engage, engage for something like two years and then come inbound. They were ready, they just weren't raising a hand. Starting small with two BDRs We had two BDRs at the time, and didn't want to go hire more on a hunch. My pitch was: give each of them one asset from a campaign we were running, add a little scripting and a little sequencing, and see if their efforts matriculate through to SQLs. If they do, we hire more BDRs and run more of that type of campaign. It worked. People booked meetings and those meetings moved through. And even when a deal didn't close, if you picked up the phone and called those people back three months later, the ones who'd consumed the content were very often ready to buy. We called it Allbound. Adding signals Allbound only reaches people who already know you, and this is a market where a lot of buyers don't know a solution exists. They are generally NOT software buyers and they usually have to go find budget (they don’t have it). Having AEs do cold outbound on top of all their inbound didn't make sense, and our BDRs were junior, so we built signals specific to our ICP. Clay was new at the time, and we worked with a GTM engineer (before that was an official title) to scrape for recent acquisitions, corp dev job postings, new corp dev hires, and recent PE funding, with gates on company size so we weren't targeting the whole world. The ICP-specific signals cut prospecting time way down for the BDRs. On top of surfacing the Allbound folks engaging with content, they surfaced prospects who didn't know us yet. Scaling it Once the pilot proved out, we built the BDR team. Alongside this, our growth marketer vibe coded Lovable interactive experiences and hooked them up to our website tracking: a build-your-own diligence checklist, a checklist grader, and a "what's your M&A personality" quiz. They performed really well, and the BDRs thought they were fun, which made calls super natural. "I saw you did the personality test, who'd you end up with?" We tracked inbound, outbound, and Allbound SQLs and first booked meetings every week. That mattered because outbound SQLs took a lot longer to close, and my VP of Sales and I couldn't guarantee they'd close in quarter. I needed the mix so nobody looked at that pipeline and decided it wasn't good. Results Our pipeline mix went from ~90% inbound, which was never going to last, to roughly 40% inbound, 40% outbound, and 20% Allbound. At first the lower inbound percentage looked scary. But inbound wasn't shrinking. Everything else was growing around it. SQLs went from about 63 a quarter to 150, and for the first time we had channels we could actually scale instead of waiting on hand raisers. Key metrics Pipeline mix: ~90% inbound to ~40% inbound, 40% outbound, 20% Allbound SQLs per quarter: ~63 to 150 BDR team: 2 to 7 Allbound-sourced pipeline or win rate: 18% win rate to ~33% win rate Built with Supritha Rao, Senior Growth & Product Marketing Manager
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Validated by 3GLSRHSRebuilt Dealroom's GTM From Scratch and Grew ARR From $3.5M to $12M In Under 3 Years
When I joined Dealroom, the business was bootstrapped and the founder had taken it to about $3.5 to $4 million on his own. He'd brought in a new COO, Greg Lord, because he knew he'd hit a ceiling with the way he was doing things. I was brought in to figure out what go-to-market actually was, and then pour gasoline on the right things. Two problems were obvious right away, the existing team wasn’t structured correctly and we didn't know what we should be doing next. Dealroom is an M&A platform,essentially a CRM for people doing deals plus a secure data room, and we were selling everything to everyone. There was no ICP. The founder had a great podcast (still the top podcast in M&A) and a lot of great starts, but things were piecemeal and measurement was scattered as a result. No definition of an SQL, no campaigns, no sense of how things were matriculating through the pipeline, and most importantly - no clear ICP. To give you a sense of the ICP problem: there's corp dev at Salesforce, a massive team with in-house tech and crazy buttoned-up processes. And there's corp dev at a PE-backed lawn care roll-up, with a heavy mandate to acquire, no systems, and very limited budget. We were selling and messaging to both of them exactly the same way. Finding the ICP We leaned on Geoffrey Moore's Crossing the Chasm. His point is that to cross the chasm you have to niche down, and he compares it to lighting a campfire: you light one piece of newspaper, it catches the next, and eventually the whole fire goes. We needed to find our first piece of newspaper. I ran a multi-day exercise with our CEO, our COO, our VP of Sales, our best seller, and our head of CS. We went through every customer and ranked them by who had the biggest pain and where Dealroom was most likely to solve it. This was before AI, so we pulled some HubSpot data and then manually filled in company size, revenue, and industry for everyone. Running this today would be much easier and faster with the Hubspot MCP + Claude. Out of all the ranking and back and forth, we landed on a clear ICP: PE-backed roll-ups doing 3+ acquisitions per year in North America. Rebuilding the positioning around pain I came up through product marketing (Salesforce, then building PMM teams), so my move was to go straight into positioning and messaging. What Dealroom was saying wasn't wrong. It just wasn't differentiated, and it wasn't speaking to that ICP. Nothing we were putting out would "stop the scroll." If you were in corp dev and saw it, you'd think, meh, okay. I interviewed a bunch of customers, and I listened to individual Gong calls filtered by prospect type. I'm a big believer in aspirin versus vitamin messaging, something I learned from Greg. You don't need a vitamin, but you need aspirin. So I dug into three layers: what are your pains, what's the negative business impact of those pains, and what does that mean when you're talking to your CFO, who is the final decision maker. That last layer is where a lot of messaging falls flat. People stop at the pain and never tie it back to the business, so the champion can't sell internally. We worked it all the way through. Dealroom makes you faster. Okay, so what does that mean? I can do more deals. How many more in a year? What's your PE target? Now you can talk to a CFO and sell the positive business impact of DealRoom Testing it with sales first My first step was to test the new messaging with the sales team. I'd built it alongside our VP of Sales and the sales and CS folks who were most involved, so we enabled the team on a core slide deck, had them pitch it to prospects, and watched what stuck. We learned a ton and made a lot of tweaks. From there we pushed it to the website, starting with the homepage, then the platform and pricing pages since those were our top pages. We watched conversion to make sure nothing dropped. It didn't, and we saw positive momentum. Only after that did it go into paid social, email, and the video content we were doing on YouTube. Building it with sales instead of handing it to them mattered a lot. At a company this size there's no space for marketing and sales not being aligned, because it just blows up. We created key alignment and good will that stands to this day between teams. It bought sales in on what marketing could do. Building the measurement layer We rolled out campaigns, UTMs where relevant, basic reporting, and lead scoring to lay the foundation. My team owned the full pipeline number (sales qualified leads), not just marketing-influenced. I think it's silly to only own marketing, and owning all of it meant our starting point with sales was always "if inbound is down, how can I help you with outbound?" Results In my time at Dealroom, ARR grew from about $3.5 million to $12 million. Our quarterly new bookings targets went from around $400K to $500K when I started to about $1 million when I left. SQLs went from about 63 a quarter to 150 per quarter. Figuring out what to sell was a big part of it too. We used to sell a single piece of the platform on its own, and those customers would churn. We stopped. Q1 this year was a tough retention quarter because of all the non-ICP customers we'd sold to earlier, but by Q2 and Q3 things had leveled out. Obviously this feels tough initially to a sales team, but they are now seeing that selling to the right ICP meant bigger, multi-year deals. I can't take all the credit. We had a great new sales leader, a great sales team, and CS figuring out their part. But it started with getting focused on who we were for. Key metrics ARR: ~$3.5M to $12M SQLs per quarter: ~63 to 150 Quarterly new bookings target: ~$400K to $500K to ~$1M
Not validatedGrew bootstrapped business revenue from $3M to $12M in under three years
I was brought in to rebuild the marketing organization and GTM engine at a bootstrapped M&A software company. The business needed a stronger pipeline engine and a clearer go-to-market strategy to scale beyond its early revenue base. I evaluated and rebuilt the marketing org with a team of AI-first marketers, redefined our ICP and GTM strategy for a niched-down target market, and overhauled our product messaging and positioning, activating it across marketing, sales, and customer success channels. As a result, we grew the business from $3M to $12M, more than 3x growth in less than three years, while also driving 180% growth in pipeline generation and a 67% lift in win rate from SQL to closed won.
Not validated