Max Wrote $20k Check to Invest in Outreach.io At $3.5m Valuation, Today North of $60m in ARR
How Max Built and Sold SalesHacker to Outreach In a Very Short Timeframe
Unique Ways Max is Managing Remote Company during COVID Lockdown

This is an AMA session with Max Altschuler, Founder of Sales Hacker, the world’s largest network for B2B Sales professionals. Max was an early investor in Outreach.io ($20k check at $3.5m valuation) and now is VP of marketing at Outreach.

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Question: Hey Max, it’s AMA time. Tell us sparknotes on your story. How did Sales Hacker originally come to be?

Altschuler: Oh man, long story but basically I was hacking our own sales process at Udemy and then turned it into a meetup, then that became a conference, then that became a publication, then so on.

Question: Hey Max, here’s a question for you, what were some of the unique challenges that came with integrating a ‘media and community’ company with a SaaS company? While obviously the Sales Hacker brand was kept separate from Outreach, what changed behind the scenes?

Altschuler: Heyoo! I’ll hit that question first. It’s hard!

Altschuler: The first thing you want to do is change nothing. You need to maintain the trust you’ve built up over time as a standalone company not owned by a vendor. Our mantra was you wont see anything new that negatively affects the reader/listener/viewer/subscriber experience. Over time, you can start to evolve things but I’d wait at least 6 months.

Altschuler: We still to this day have separate MA/CRM instances and Outreach only gets data or leads the same way any other vendor would. By sponsoring. However, we don’t charge Outreach and they get the remnant inventory from time to time. We’ve been able to leverage the value we provide with Sales Hacker in deal cycles as a value driver. So we do that.

Altschuler: After 20 months, we are finally starting to make more material updates and changes which you’ll see at the end of this month with our community feature roll out.

Company Max Founded, SalesHacker, Gets Acquired by Outreach

Question: Hi Max, what is the primary strategic advantage for Outreach acquiring Sales Hacker? and How specifically does Sales Hacker add to the overall vision of Outreach? Where is the link?

Altschuler: Rising tide lifts all boats. So that’s the first thing. Sales Hacker’s goal was always to educate the market on modern sales trends and leveraging tech in the sales process. So the more companies we can help modernize, the more money will be invested into the stack.

Altschuler: In general, you’re much more likely to buy from the company you learn from than another vendor, so that’s the link. We will, over time, make it more Powered by Outreach.

Altschuler: We also use it as a value drive in deal cycles. We sell to Sales, so offering a CRO/VP Sales a spot on a podcast for a brand they know that gets 20,000 downloads is a great value driver no other sales vendor can provide and it opens up that relationship at the exec level now.

Question: Hey Max, thanks for being here! Have a slightly open ended question but am curious to get your take – when a startup moves from founder-led sales to making their first official salesperson hire, what advice do you have? What missteps have you seen companies make when undergoing this sales transition?

Altschuler: Don’t hire the transactional sales person that’s used to having the big logo and team and sales enablement function behind them. Hire the scraper that can get creative. You are mostlikely still in product market fits stages then. You need someone who can help adapt on the fly. Try to find someone that’s either an sales side entrepreneur or has done early stage before successfully.

Question: Hey Max, Romain from SEO Buddy (MVP launched 2 months ago, only 4 Paid Users). What is your favorite “hack” when you’re still looking for your product market fit to get lot of “Prospective User” to interview and find quickly your ideal Buyer Persona?

Altschuler: Go find customers from complimentary or competitive products and prospect into them via email or linkedin. Try to build some sort of educational material that would be your hook to get them to learn more. Something unique. You can find these folks usually on their websites. i like to have a team of virtual assistants build lists for me be scrape sites and LinkedIn headlines/titles.

Question: Whats an example of educational material you sent in early days?

Altschuler: An example could be an really good ebook. or one pager even. Or data driven content like Gong does really well with Gong Labs. Something unique.

Question: Here’s one I’m curious about: Lots of angel investors in this group. How’d you spot Outreach early on and decide to angel invest? I’m assuming that also set the stage for your eventual exit to Outreach? How much did your dominance as a distribution channel (SalesHacker) for tools like Outreach drive the acquisition versus your angel relationship with Manny?

Why Max Wrote a $20k Check To Invest In Outreach.io at $3.5m Valuation

Altschuler: I met Manny in Union Sq for a coffee (I had an OJ) back in Dec 2014. i was a big Toutapp power user and on their site. TK is still a good friend. i knew all of the players in the space. But nobody was really approaching it the right way until i heard how Manny was doing it. He was a seasoned product guy (AWS/MSFT background), and had a killer onboarding flow.

Altschuler: Manny is also an immigrant. Russian and Ecuadorian. Guy doesn’t take no for an answer. i basically cut him a check on the spot. It was my first investment. i called my dad who is a financial advisor (thus my financial advisor) and he thought it was silly and risky of course, but i convinced him i was going to do it anyway and he said fuck it, I’ll match you if he’ll let me. So i tease my dad that i paid him back from my up bringing now. We’re even, haha.

Altschuler: Anyway, it had nothing to do with the acquisition. I kept a spreadsheet of companies that could potentially acquire us. I updated it as i went. It was broken up by industry (SaaS, R&A, Consultants and Trainers) and had company. contact name, and relationship strength. I went to Unleash and had 15 min to catch up with Manny.

Altschuler: He just raised a $65m Series D. i said congrats, what keeps you up at night. He said Marketing. I said well i built a media company for B2B Salespeople. You have the product, i have the audience. Let’s do this thing. We went fast into diligence from there and deal was done in 3 months. i shopped it a little bit but Outreach was the best fit and highest upside and ready to move asap.

Question: What was size of the original investment you made in Outreach?

Altschuler: $20k on a $3.5m pre.

Question: Interesting that you built the company with an ‘acquisition mindset’ like this. Do enough founders think about this early on? Or is it distraction?

Altschuler: I didn’t build it with an acquisition mindset per se. i ran it for 5 years as stand alone. i got my first offer maybe 3.5 years in. At that point i realized i needed to be prepared and that i had something acquirable. YOU NEED TO BE PREPARED. Honestly, everyone should have their books ready, their acquisition deck created and updated monthly, etc. You never know when an oppty will arise and it’s not that hard to maintain. But it could blow it for you if you dont have your shit together quick enough. Seen it happen

Question: Hey Max, know that Sales Hackers pivoted at a point in time from in-person conferences, to being fully digital as you said it is “more scalable, trackable, and targeted than in-person events.” With companies now having to go digital by necessity, what advice do you have for other companies going through this transition from in-person field marketing/events to digital media + digital community?

Altschuler: Start doing digital asap if you haven’t already. Even if the audience is small.
I started the SaaStr Annual for Jason Lemkin so he became a bit of a mentor for me. i met with him in 2017 and told him i was worried about the events business and what to do next and he said just grow man. Grow your list. Once the list was like 30k, we had enough to get 150 people to come to webinars. That meant we could charge sponsors. Now we have 160,000 person list and webinars get 1200-2000 reg per. 2x per week. Here’s example: https://www.saleshacker.com/lp/tips-sales-success-linkedin/

On Running Company Remote During COVID

Question: With more companies going remote (pre and post-pandemic), what advice do you have for building a remote sales team?

Altschuler: Get Outreach (our something that helps you ramp reps and track/adapt as you managed them). If possible, hire people who’ve done sales remotely before. Weekly stand up meetings are even more important than before. Maybe add a second. Weekly office hours for deal inspection. Cross team collab is key. Revisit how Sales and Marketing, Sales and Product are communicating. Maybe create a knowledge base for it or a center for content/updates if you dont already have one.

Question: It’s been quoted that you “used SEO to get acquired.” What was your strategy here?

Altschuler: Hire Gaetano DiNardi and get out of his way. Seriously though, spare no expense in finding a legendary SEO full time employee and hire them. They’ll be accretive.

Question: Thanks for joining us today! My question is – which sales/marketing channels you would focus today on $10k – $100k monthly MRR?

Altschuler: Totally depends on the business. Hard to do blanket advice here. Good content/SEO will drive inbound. Thats the basis for a good strategy. Can run paid ads off that. Or have reps use that as value drivers in outbound. Would look into testing both directions.