VP of Marketing at DealRoom

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.

Validators

Macy Wilcox

Customer Marketing Specialist

Peer

I worked at Dealroom as a Customer Marketing Specialist on the marketing team Hannah Jarrett led as VP of Marketing. Although I did not report directly to Hannah, her leadership shaped my work and how our team operated. What stood out most about Hannah was her driven mindset in work and personal life. I saw that firsthand as soon as I joined the team; she always pushed us to take on new tasks, even when challenging, and helped guide us throughout the process. She was constantly finding new ways to learn and push each other, all while making it such a fun experience. Her Claude "Lunch & Learn" and Creative Corner during our marketing team meetings were personally some of my favorite moments. Lunch and Learn was something Hannah took charge of, ensuring everyone knew all the necessary or fun creative skills you can use with AI while making it a fun workshop for the company. Creative Corner was a fun segment of our weekly marketing team meetings where we would all turn our creative minds on and help each other with any brainstorming of swag, projects, campaigns, etc. It was a fun part of our meetings where we could help each other with whatever we were working on, and any idea was welcome. Working with Hannah and the team she helped shape into driven, confident, and creative marketers, even for 3 months, was an experience that not much can compare to for the rest of my life. She is always a smiling face to see first thing in the morning; she pushed everyone, even on other teams, to be the best version of themself, and when doing a task/project for her, she knew how to provide amazing feedback in an honest and helpful way. As a junior team member, she made me feel like a part of the team. Within my first week, she made me understand the importance of the why, messaging, and working with a team that I will take with me forever. Any team would be lucky to have Hannah as a leader, from a great mentor to your biggest supporter in all aspects of the job and life!

Macy Wilcox

Customer Marketing Specialist

Peer

I worked at Dealroom as a Customer Marketing Specialist on the marketing team Hannah Jarrett led as VP of Marketing. Although I did not report directly to Hannah, her leadership shaped my work and how our team operated. What stood out most about Hannah was her driven mindset in work and personal life. I saw that firsthand as soon as I joined the team; she always pushed us to take on new tasks, even when challenging, and helped guide us throughout the process. She was constantly finding new ways to learn and push each other, all while making it such a fun experience. Her Claude "Lunch & Learn" and Creative Corner during our marketing team meetings were personally some of my favorite moments. Lunch and Learn was something Hannah took charge of, ensuring everyone knew all the necessary or fun creative skills you can use with AI while making it a fun workshop for the company. Creative Corner was a fun segment of our weekly marketing team meetings where we would all turn our creative minds on and help each other with any brainstorming of swag, projects, campaigns, etc. It was a fun part of our meetings where we could help each other with whatever we were working on, and any idea was welcome. Working with Hannah and the team she helped shape into driven, confident, and creative marketers, even for 3 months, was an experience that not much can compare to for the rest of my life. She is always a smiling face to see first thing in the morning; she pushed everyone, even on other teams, to be the best version of themself, and when doing a task/project for her, she knew how to provide amazing feedback in an honest and helpful way. As a junior team member, she made me feel like a part of the team. Within my first week, she made me understand the importance of the why, messaging, and working with a team that I will take with me forever. Any team would be lucky to have Hannah as a leader, from a great mentor to your biggest supporter in all aspects of the job and life!

The Pain Campaign: 50 Halloween Mailers Drove 5 Deals & What I Changed the Second Time

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Validators

Macy Wilcox

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Macy Wilcox

More from Hannah

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