An Ode to Sales Hacker (RIP)

Last week we announced that my new company, the GTMfund, has acquired my old company, Sales Hacker, from my…other old company, Outreach.

It’s very unusual that when you sell a company, you get a say in what happens after that. I’m incredibly grateful that we were able to decide its future and ultimately lay it to rest. It deserved a proper storybook ending.

I’ve gone through a mix of emotions, reliving the insane 10-year journey that came out of a young Max being naively intellectually curious about how to scale sales at a startup. My life was taken on a wild journey, where I had the chance to meet and hopefully positively affect the lives of hundreds of thousands of people.?

So I figured it was only right to pen this ode to Sales Hacker, even if I’m the only one who ever reads it or appreciates it. At least I’ll have it. It truly changed my life.

Beginning:

I began my career at a startup in San Francisco called Udemy. This is when startups were for nerds, and Ivy League grads were still going straight into investment banking instead of SaaS sales.?

I was the eighth hire and the first person focused exclusively on scaling the sales side of the business. We didn’t have a lot of funding, and I had no idea what I was doing. But I was entrepreneurial and had a brief track record to prove it.?

In college, I started two companies. The first, I won a university grant for. The second was profitable and my cofounders and I ran it from Costa Rica and Nicaragua. I actually had my first job interview with Udemy from a payphone call center outside of Grenada, Nicaragua.?

I got the job and locked in. Worked non-stop to prove myself. We did some hacky stuff, turning virtual assistants in the Philippines into SDRs, leveraging ToutApp (one of the first sales engagement platforms), and building web scrapers via Upwork to assemble endless leads lists.?

Other founders and VCs would ask our founders and VCs what we were doing to scale sales, and those questions would be passed on to me.

There was demand for this knowledge, as well as an inflection point in the market. New sales tech was finally getting investment. Startups needed to figure out how to scale sales while dealing with finite resources.?

I started writing about my sales hacks on my first blog, maxtalkshacks.com. I had no audience, but I wrote everything out so I could send it to folks when they messaged me about what we were working on.?

This led to a few of us starting a private meetup we called the Sales Hacker meetup. We met monthly at a place called The Factory, which was like an early WeWork. These meetups grew from four people to about 20 over the course of the first year.?

The meetups led to our first-ever, 300-attendee Sales Hacker Conference in San Francisco in September 2013. This is when I officially started the company. The first event made a profit of more than my annual salary at Udemy and only took me six weeks to organize. Then we did a New York conference, launched the online publication SalesHacker.com, and organized paid public meetups in over 20 cities across 5 continents.?

I wrote Hacking Sales, a book about leveraging technology to generate more revenue with fewer resources. It was touted publicly by Sam Altman (YC/OpenAI) and Justin Kan (YC/Twitch), amongst others, as the go-to book for building a sales function at startups.

I wrote all 28,000 words in 5 days, pulling 18-hour-a-day shifts, from an island off the coast of Bali. It sold over 35,000 copies in the first year and was subsequently re-published by Wiley. It pulled all of my wisdom on this topic into one place. Being younger in age for my audience, the book added some much-needed credibility.

One day, I got an email from Jason Lemkin, who was a speaker at our first conference and really grokked what we were doing. He had this amazing Quora feed that he wrote under the brand SaaStr. He asked if I could help him start the SaaStr Annual, an idea for a conference that he had around his SaaS experience through selling EchoSign to Adobe.?

I said yes. We organized the first two events for him - 1000, and then 5000 attendees. The cash flow from those events helped us hire and go bigger earlier at Sales Hacker. Today, SaaStr is a massive business and I couldn’t be happier for Jason, who has given so much back to the SaaS community.?

The experience with SaaStr opened up a whole new network to me as well as a much bigger way of thinking.

We tried to figure out how to broaden our own events at Sales Hacker, organizing Sales Stack and Revenue Summit. We even did a joint event with Salesforce for two years called Sales Machine. A lot of lessons were learned the hard way on how to work with large enterprises. Looking back, I’m so appreciative of the learnings and the chance to work with them.?

We brought in bigger named sponsors and grew the brand beyond startups. One of my favorite memories was the Dreamforce hack. We found an apartment complex on the corner of 3rd and Mission overlooking Dreamforce. We realized if we rented an apartment in the building for a month, we could use the common space at an hourly rate.

For a few years, we rented a corporate apartment in the building for a high rate, about $10k per month. Then we would throw an event for three days in the common area and sell sponsorships. We ended up with our own Sales Hacker event at Dreamforce and it was profitable!?

The last year before the Outreach acquisition, my appendix ruptured on Friday before the Sales Hacker event. But I didn’t want to miss it. I showed up on Monday and worked the conference for all three days. At the end of each day, I would change my shirt and there would be blood around where the stitches were.?

Eventually, the conference business got too tough for us to compete. When we started in 2013, you needed a lot of customers to do your own customer conference. By 2017, startups had raised so much money, they all started doing their own customer conferences early in their company existence. All of a sudden, we had a lot of competition. The writing was on the wall that these events were going to be harder to profit from. The juice wasn’t worth the squeeze.?

That same year, we started to do medium and large-scale webinars and virtual events. We were one of the first to pioneer this. They were wildly profitable and grew our list. But the business was in a tough place and we were hitting up against a hard ceiling.?

How could we go bigger from here? We had an extensive list of subscribers and a profitable digital events business, but it just wouldn’t be enough.?

Middle:

I had a decision to make. We started exploring what other business lines we could spin up. Courses, paid communities, analyst/research reports, etc. Nothing sounded super interesting and everything would take significant time and resources.

At the same time, I had a CRM of potential acquirers that I kept up to date. We had some active conversations that came inbound to us, but nothing that really materialized.?

In 2018, I went to Outreach’s Unleash conference. I was an early investor in Outreach’s pre-seed round, so I was able to get 15 minutes with Manny, Outreach’s CEO, at his customer conference.?

I said, “Congrats on the $500m valuation Series D round of funding. What keeps you up at night?”?

“Marketing,” he answered.?

I said, “I have the number 1 media company in sales and you have the best-in-class new sales tech company. Let’s make something happen.”

We got a deal done three months later and announced it. Between the initial conversation and the deal getting done, I started working and they made the call to install me as the VP of Marketing.?

I was thrown into the fire, having never run marketing before. Overseeing a massive team, reporting to the CEO, presenting to the board, rolling up to a big number -- I’d say my head was spinning but my head had no time to spin.?

I did have a secret weapon though. I knew this audience better than anyone. On top of that, I inherited an amazing team and we hired A+ folks over the following months. The business was moving insanely fast.?

This was my favorite time at Outreach. The pace of business was like nothing I had ever seen. The first year was a blur, but business growth was beating our incredibly lofty expectations.?

My first call with the marketing team was before I started. I asked about the lay of the land. What’s on the calendar that we need to be cognizant of? How are we thinking about category creation and the brand? What’s working and what’s not? Etc etc etc.?

It became super clear that what the Sales Hacker team brought to the table was exactly what Outreach was missing. We needed to put Outreach and Sales Engagement on the map. To do this, we needed to put community at the center of everything we did.

We had only ten weeks until Dreamforce. Outreach paid for a booth, but had nothing planned yet. And we had our conference in eight months, also with nothing planned yet other than the down payment. The previous event was over budget considerably. So I asked the team who we used for event planning and they gave me the name of a person and an agency.?

I set up a call with them. After the call, I called the individual on her cell which was in her email signature. I just said, “We are about to do a ton with you, but I’d rather you work here. Come in-house and the agency you currently work for will still win because we will still use them for both events. But we need someone in-house, so if I don’t hire you, I need to hire someone else and they may choose a different agency. Let me know.”

She and I officially started at Outreach on the same day.?

Outreach was creating the Sales Engagement category alongside some hard-charging competitors. Our big category creation lightning strike was that we bought SalesEngagement.com and launched the Sales Engagement Podcast at Dreamforce, with our book titled Sales Engagement coming out at Unleash six months later. I called my publisher at Wiley and got us a book deal. The only catch was that in order to have a copy on every seat at Unleash, I needed to write the book in a month.?

We used the same process I put into action with my first book, Hacking Sales. Over 30,000 words were stitched together in under 4 weeks. I wrote about 15,000 of them over 3 days during the Thanksgiving weekend. The rest we sourced from customers and employees including pieces from Manny and Mark Kosoglow. Jade Makana was a huge help here.?

Unleash 2019 was a whole new event. We doubled the audience size to 1200, 4x’d revenue, and cut costs by two-thirds. We had a book on every seat for the opening keynote. We had an entire expo called Outreach Galaxy that was the main focus of the keynote. You could now prospect accounts across multiple channels all through the Outreach platform. Shout out to Stephen Farnsworth for the hustle on this.?

It was a rush! And best of all, the business was blowing out its numbers.

The Sales Hacker integration into Outreach’s core business worked really well too. It was a massive supporter of the business objectives without leaving the community feeling like it became “corporate” or “commercial”.

Outreach employees embraced the Sales Hacker team and asset with a deep understanding of how it could help them accomplish their short and long-term goals. I have to shout out Jordan Greene, Harmony Anderson, Mark Kosoglow, Matt Millen, Andrew Kinzer, Rajeev Batra, and Anna Baird, for their collaboration and empowerment during that whirlwind period.

During my time at Outreach, we more than 10x’d revenue. Our valuation 9x’d (more if counting secondary offerings at market peak).

Sales Hacker was a business for a decade. I was there for all but the final year. Much of our success came from the team we assembled, especially in the early years.?

We hired stretch candidates for everything. Leah Kahn ran our early events, Jake Spear managed sponsorships, and Jack and Alicia Kosokowski’s agency supported us in marketing. Our virtual assistants in the Philippines led by Joan Mirano and Maricel Roma. Then came the game-changing addition of Gaetano DiNardi, Alina Benny, and Josh Giardino. And finally some key hires in Scott Barker, Sydney Abrams, and Colin Campbell.?

I have such fun hiring stories for all of them. Looking at each of them now, they’ve proven beyond Sales Hacker that they are truly exceptional talents.?

The community really rallied behind us early on. Slowly but surely, we won folks over. Too many folks to name, but you know who you are. I appreciate you big time.?

End:

A few months ago, I heard a few SaaS companies inquired about buying Sales Hacker from Outreach. It’s a tremendous asset but needs TLC. A lot of times in business, when the founder leaves so does the soul and vision.

Outreach itself has a massive vision to execute on and Manny is the right leader to continue driving it to the next level. But from the outside, the Sales Hacker area of the business seemed a bit lost.

I made an offer and made my case. If we could get it for a really killer deal, it was worth it.

I thought it was important to buy back Sales Hacker for two reasons.?

1) The points I laid out in our article on the GTMfund last week. This acquisition will help us scale the media part of our Fund/Media/Community flywheel.?

2) I didn’t want the community to fall into the wrong hands. Sales Hacker is a big part of my legacy. I birthed it. I felt like I was responsible for it, even if I no longer owned it.

While we aren’t going to be the suitor offering big bags of cash, Outreach -- a high-integrity organization -- understood where I was coming from. Ultimately, we were able to come to terms. As you can see from the announcement video with Manny and me, we are both still mutual supporters and look forward to continuing that going forward.?

So RIP, Sales Hacker. If you have a great story from your experience with the company, I’d love for you to share it here on LinkedIn.

I’m really excited about what we have in store for you with GTMnow and feel immensely grateful and fulfilled with my work at the GTMfund. It’s been a blast and I can see myself doing this for the next few decades. I really think we’re onto something special and we have the supporting team in Paul, Scott, Sara, Joan, Amit, and our LPs to take us far.?

Stay tuned for the launch of GTMnow next Tuesday, August 15th!