So You Saw The News...

As you may or may not know by now, this week Sales Hacker was acquired by Outreach.

If you look here, you can read all about the announcement, how we plan to keep Sales Hacker separate and evolve it in ways it couldn’t have been evolved before, and what I’ll be doing for Outreach going forward.

But what we didn’t talk about on the Sales Hacker blog that I want to discuss here is my “Why”. The personal decisions and how I think about my career, my life, and the future. I’m super self reflective if you couldn’t tell from the two books I wrote (Hacking Sales and Career Hacking for Millennials), so I thought I’d share a bit about what went into my thought process.

Part I: Why Outreach?

First things first, why Outreach?

We had a lot of options, which I’ll get to later, but as I alluded to in my Sales Hacker post, Outreach is at a point in which they are truly creating a category, not just a product. Sales Engagement or whatever you call the category, is real. There will be multiple winners, similar to the Marketing Automation outcome where you saw Hubspot, Marketo, Responsys, ExactTarget, Eloqua, and many more have incredible runs (that are still continuing in many ways).

The pulse is strong. They’ve grown from $0-$30m in ARR in ~3 years and will still double annual recurring revenue this year. They also raised over $125 million in funding from top tier and strategic investors including Microsoft, DFJ Growth, Spark, Sapphire and more, recently valuing the company at over half a billion dollars. If things track the way they currently are, an IPO is ~2 years away.

Exec Team and Past Knowledge

I was actually one of the earliest investors in Manny and team. I know the founders well and love how they approach thinking through the problems that salespeople and sales leaders incur day in and day out. It’s funny how things come full circle like this!

We at Sales Hacker, have worked with the executive team, sales team, and marketing team for a while now, so we know their high level of focus and competence. It helps that they’ve been able to hire A++ talent across the board (I’m hiring btw!). The more team members I met, the more this is reinforced.

Product and Customer Success Led Organization

One of the reasons I invested in the first place. I think the foundation for a scalable company is rooted in product and support. Our key strategic objective is making sure customers absolutely love our platform. This means giving customers an amazing experience from day 1, and then building on it as we go. The product is what we sell and how we sell, so naturally Sales and Marketing will be crafted appropriately and take care of itself after that.

It’s one of the first companies I’ve seen where the product is ahead of Sales and Marketing. Meaning when they are promoting it or selling it, they can actually do it right now. Whereas some organizations promise and promote things that are on the roadmap but are not actually possible to do yet. That’s a salesperson and marketers dream.

The platform is better than I realized and is evolving rapidly. Once I saw the roadmap, I knew they were about to take a few huge steps ahead of the competition. Well researched and well thought through developments in voice, text, LinkedIn, scheduling, revenue attribution, security, deliverability, and so much more are coming and coming quick. If you’re a Sales Development Rep, Account Executive, or Customer Success Manager, or manage them, you should definitely speak to your rep at Outreach asap and have them walk you through it. Or ping me and I can help.

Perfect Ying Yang of Competencies

Outreach has an amazing product, product team, sales org, customer success org, support org, and everything else you want in a company, but has never been a company known for marketing. We’re largely a company known to be able to sell and market.

Over 150 companies in the past 12 months have basically used us as outsourced CMOs. We help with much more than just the coordination of webinars. We usually help build the narrative and source the talent too. So if you match their core competencies with our ability to understand salespeople and market to them the way we’ve been able to, it has the makings of a beautiful match.

Legacy and Sales Hacker

This is one of the most important pieces to me. They were 100% behind making sure nothing about Sales Hacker changed. No Outreach branding, no advertisements, and no salespeople putting their hands in the Sales Hacker database cookie jar. Sales Hacker no longer needs to rely on revenue, so it will allow us to build the best community and deliver the best content experience possible.

I’m also able to keep writing and pushing my books and thought pieces (like this one), continue my investing and advisories, speak at events on my own behalf, and continue doing some of the things that give back to the community that are my own. These are my passion projects.

Future of Sales

I’m more passionate than ever before about the sales profession and my ability to impact the lives and careers in it. We were always missing the big piece of the puzzle at Sales Hacker, and now we have it. The best in class platform for supporting the future of sales at companies across the globe, no matter the size, cultural differences, segment focus, or any other variables.

We are in the early days of modernizing the profession, and as buying continues to rapidly evolve, so should we. It’s an exciting time to be in sales.

Part II: Why Would I Want to Change My Lifestyle?

This was a really tough decision, but not for the reasons you might think. Over the past few years, I lived the ultimate work life balance. Well, maybe a little more living than working. Our whole team is remote (and will stay that way) so I was able to spend weeks at a time traveling around and living in places like Australia, Singapore, Thailand, Hong Kong, Dubai, Colombia, Mexico, Cuba, Brazil, Argentina, the Caribbean, Ireland, Scotland, England, Croatia, Greece, Sweden, Denmark, France, Spain, a month in Japan, a month in Italy, the Philippines, four Decembers in Bali, a week in the Maldives, Iceland, Alaska for the Northern Lights, the Grand Canyon, a winter in Miami, few week stints in Hawaii, Sedona, Maine, Phoenix, LA, SF, and NYC sewn in there, and a few summers living full time in the Hamptons. All while building this business (and others). And these are just the places I went that I worked from during the past four years!

Going back to full time work for a thriving company doesn’t mean the travels have to stop, they’ll just have a different purpose and different timing. And if all works out, I’ll be able to feel fully comfortable doing it in a couple short years.

Learning

A few months ago I felt like my learning had stalled a little. I was becoming complacent and honestly, I’m not currently wealthy enough allow that. I feel that if you keep learning and growing, you’ll always be able to make money, no matter what direction the market is going in. I think that unless I have $20 million in the bank, I can’t afford to keep resting on what I already know. I needed to round out my skill set.

This is one of the reasons I started SUTRA and got into advising companies. To accelerate my learning on Sales Hacker would’ve meant to create a new line of products or pivot the business. We kind of got to a point where if we wanted to do that, we would cannibalize our business.

If we ditched “good” to go for “great”, we’d have to kiss “good” goodbye. It’s tough to say see ya to a cash flow business without knowing what the upside might be. Which brings me to…

Upside & Security

I was building a cash flow business and doing pretty well on annual cash flow. Last year we successfully transitioned from an events business to a digital business, which has much better margins. We were tracking to $3m in revenue with a lean and fully remote team of employees and contractors spread out across the US, Canada, India, and the Philippines. I definitely did not need to sell the business.

I took nice trips and made a few investments in other personal projects including starting SUTRA. Things I can still do. I was able to write two books, which I can also still do since I wrote them both in under a week (from Bali).

Over the next 2 years, this deal will provide me with similar cash flow to what I had recently at Sales Hacker, while providing me with stock that has far more upside in a shorter amount of time and has a real chance to get me to my comfortable number upon exit.

Being well VC backed and a healthy business, this deal should provide some security in the case of a recession, which is something I was spent time worrying about as a bootstrapped business owner.

It was also very important to me that my team was happy with the deal. Everyone that works for Sales Hacker gets raises and other benefits, plus a new set of learnings and a bigger team to be a part of. It was easy to see that this is a great addition to each of their career arcs and will work for them in the long term too.

Opportunities

Over the past 4 years, we had plenty of other opportunities to take Sales Hacker in a different direction. There were other acquirers we were talking to. We could’ve started a Sales Hacker VC Fund. We could’ve built an upsell like consulting or training or research advisory. We were even looking at rolling up companies into our own suite of technology.

I’ve looked into everything. Ultimately, this gave us the best path to make a big impact, very quickly, with huge upside and a lot lower risk.

The other issue with opportunity is that sometimes because you have some many options, it can almost paralyze you from making a decision on what’s best to do. We were at a good point in our business where it was time to pick a play.

Gratefulness

It’s an exciting time and I’m super grateful to everyone who has supported us over the past few years. I’m grateful to my team - current and past, our supporters, all of the learnings (even the hard ones) along the way.

It’s been fun, and we’re only just getting started. Stay tuned!

Your friend in Sales,

Max

Ps. We’re looking for a kick ass Revenue Ops/Marketing Ops hire. Ping me if you know anyone!

Pps. Thoughts or ideas for what sort of content you want to see on Sales Hacker, let me know!

Ppps. Interested in taking your sales team to new heights? Let’s get you on Outreach!