Sales Hacker’s Max Altschuler on selling more with less

How can you capture, qualify and convert the right leads for your business while working within your means? Max Altschuler has made a career seeking out efficiencies in sales – hacks, as he calls them – and sharing them with the wider SaaS and sales community.

Today, Max is the CEO of Sales Hacker: a global conference, event series, and an online publication that brings together proven sales execs and emerging startup founders to share their lessons and experiences in sales automation and tech sales. He’s also the author of Hacking Sales, which includes many of the lessons he learned the hard way as an early sales leader at Udemy and AttorneyFee (now LegalZoom Local).

I hosted Max on our podcast, where he shares the strategies he’s used to grow Udemy and Sales Hacker, hiring tips for sales teams, and much more. If you enjoy the conversation, check out more episodes. You can subscribe on iTunes, stream on Spotify or grab the RSS feed in your player of choice.

What follows is a lightly edited transcript of the conversation. Short on time? Here are five quick takeaways:

1. If you’re an early-stage company you don’t just need to build a sales team, you need to build an efficient sales team. That means your focus should be on building the right customer profile and developing precise messaging to reach them.
2. When it came to finding content creators for Udemy, Max hired virtual assistants to comb sites for relevant key words and went down the rabbit hole to compile contact information in spreadsheet of potential contributors. Then, the sales team went to work.
3. When making a sales hire, Max pays attention to the way candidates approach getting the job. Do they back channel? How did they in touch with the company? In his opinion, the hiring process is a preview of their sales technique.
4. Max is a proponent of combining old-school techniques with new tools like using messengers to catch potential customers when they visit your site looking for a specific answer. It’s easier to qualify leads, and it saves time.
5. Every Monday, Max makes a list of what happened the previous week, what’s stressing him out, and what he’s grateful for. It’s an empowering way to break through malaise and see what incremental gains you’re making as a human and in your career.

Adam Risman: Max, welcome to Inside Intercom. It’s great to have you. Can you give us a quick feel for your career to date and break down your mission at Sales Hacker?

Max Altschuler: I’ve been an entrepreneur my entire life. I started a bike-share program at Arizona State University, won a grant for that and got exclusive rights to commercial bike sharing at the school. But I couldn’t raise the money for the startup; this was 2009, right after the recession. I graduated college and wanted to make American money while living abroad, so I took that entrepreneurial spirit down to Costa Rica and Nicaragua and ran a social media company from there. That was a lot of fun, but I realized we were a little too ambitious for what we were doing, so I came back and really wanted to get into startups and see how the sausage was made before starting something on my own again.

I ended up getting a job at Udemy, an online education marketplace that had just raised a seed round of funding. I thought it could turn into a big business and they needed a sales guy. I built the supply side of their marketplace and took them through their B and C rounds of funding. They’re a multibillion-dollar company at this point.

While I was there, I started really hacking the sales process. We were one of the first companies to leverage all the new sales technologies that are out there now. We built a sales development team in the Philippines, and you have to do more with less when you’re at an early stage company like that. We found a way to do it, and that eventually led to Sales Hacker.

I went from Udemy to a AttorneyFee, where I ran both sides of the marketplace. We sold the company to LegalZoom. While I was at Udemy and AttorneyFee, people kept asking me how we were growing so fast. I was sharing what we were doing on my blog at the time. I think it was called “Max Talks Hacks” back then. We started a meetup, which led to a conference, which led to the Sales Hacker publication. We helped Jason Lemkin start SaaStr Annual. We have webinars, virtual events, books – we do everything now. We’ve evolved into the leading resource for B2B salespeople who are trying to figure out how to innovate, evolve and modernize their sales processes.

I learned a ton from growing this business: about sales, about marketing, about how to run a company, and it’s been a lot of fun. I’ve gotten to work with a lot of really brilliant people, whom I’ve learned from by osmosis. And we’ve been able to help a lot of people make more money in sales, which is a profession I care a lot about.

Adam: Given that it’s the foundation of Sales Hacker, how important do you see the roles of content and community in sales today? Did you know there was an appetite for this?

You need to build an efficient sales team…you can’t just throw money or headcount at things.

Max: I always looked at it opportunistically, so as doors opened we’d see if they were worth walking through. When I started the business, there was enough momentum behind it for it to be interesting. I said to myself: “What’s the worst that could happen? I’ll do this for a year. I’m making good money off the conferences, so I know the profit is there for me. Worst-case scenario, I can do this for a year, build an amazing network and reputation, and make some money. Then I can go start my own SaaS company or go be a VP of sales somewhere at an early stage company.” I didn’t really know what to expect, and it just kept building from there. I started this about four and a half years ago, and in the time since so many companies have gotten funding that more and more companies need efficient salespeople. I think that’s the key for startups, and I think that’s really what hacking means to me: doing more with less.

If you’re an early-stage company you don’t just need to build a sales team, you need to build an efficient sales team. You need to maximize everything you possibly can to beat the competition because you can’t just throw money or headcount at things. You have to be really efficient about everything you do and be process-driven. That was the impetus for starting Sales Hacker. Today, it’s not just startups that need to be efficient with their capital and their teams, it’s everyone. We’re taking the things that we learned, and that people at startups are hacking together, and trying to make that more of an industry-wide standard.

Starting sales from scratch

Adam: You were the first sales hire at Udemy. As an online education platform, your users (course instructors) are making a big bet, where it may take a while to see results. Take us back to those early days: what were some of the most pivotal, tough decisions you had to make? Which bets you would make again?

Max: We had to pick the right categories. We were building an online education marketplace and wanted to build the Amazon for courses. In the past if you were an expert on a programming language like Python or JavaScript, a publisher would come to you and you would write a book. It was simple. There wasn’t any heavy lifting. It was very lightweight.

We had to convince people to create courses, and the timing was right for Udemy because at that point you had your iPhone and in-computer cameras that were good enough for you to record things that people would watch. It made it a lot easier for people to create courses; however, it was not even close to as easy as it was for someone to write a book. It was still this heavyweight activity, so we had to convince people to create courses for Udemy because there weren’t a lot already out there.

It was really about testing our ideal customer profile religiously, figuring out what category would pick up the fastest, and who the early adopters were. Tech was that number one place to be, so we started building our course catalog there.

It was about testing our ideal customer profile religiously.

My sales process was finding publishers who already had courses on programming languages that other people in tech would want to learn, and then figuring out how to grow from there. We asked questions like: when do you start figuring out all the areas to grow into? When you have that timing down, what categories do you open up? If you were successful in tech and you want to build this marketplace, do you try right off the bat to go for yoga courses, guitar courses, art courses, and cooking courses? Or do you keep it one chain link away from your current category?

We tested a lot of titles, and we decided it either had to be one chain link away, or it had to be something that was focused for tech people. If you taught a yoga course about posture and called it “Yoga for Posture,” it wouldn’t sell on our platform. But if we called it “Yoga for People Who Sit at Desks All Day and Stare at Computer Screens,” then it would sell to our audience. We just had to figure out the messaging, the timing, and how we were going to go about pulling our current audience into the new stuff while also selling to a new audience.

There were a lot of tough decisions we had to make and tough lessons learned in building out our virtual assistance teams and making sure that, from a cultural standpoint, people were well-trained and actually understood what they were doing. We were definitely in that startup mindset of “don’t ask for permission, ask for forgiveness.” I don’t really think that ever flies, but at the time it was a little bit more acceptable. Now, there are way too many startups out there for that mantra to still exist, because people would be running rogue. GDPR is one of those things, for example, (that would have been difficult). There were a lot of things I would probably do differently today, but it worked out for us.

A grassroots approach to finding customers

Adam: Once you get people signed up to make these courses, it’s a lot easier to retain them than to go out and recruit new instructors. What was your team’s approach to retention, and how integral was it to your success?

Max: Getting people to create a second course was part of sales. For most business models, it’s much better to get current customer to really love your product and to upsell them than it is to get new customers. But for us, the time it took for somebody to create a new course after they already created their first course was too long. We had to try to fill the pipeline with new creators, so it was just about dumping as many people into that pipeline as possible. In sales, when things are going well, it’s all good, but when things are going badly, the best cure is a fat pipeline. Get people in the top of the funnel and then you can nurture them down.

When things are going badly, the best cure is a fat pipeline.

For us, it was important to completely saturate the market. The ways that we did that were really kind of hacky. We looked for every marketplace that had content creators, and then we searched for strings of keywords using an SEO keyword generator tool. I had my VAs in the Philippines running those searches and building lists of the creators. A lot of times, they would have to go down rabbit holes. We’d say: “Go on SlideShare, type in ‘beginner Python tutorial,’ see what comes up, then scroll through their slides. Maybe they have their email address on there or their site, or maybe it’s in the description. Go to their site, get their email address, put it on the spreadsheet, fill in the other things that we need on this spreadsheet, and then that becomes our ideal customer list.”

We had SlideShare, Slide Six, YouTube, Vimeo, Google – every search-for-content site you could find, and in the keyword generator tool we’d search for “beginners, videos, tutorials” in one box and the programming language in the second box, and in the third box we’d have “introduction, advanced, novice,” and it would churn out a spreadsheet for us of all these different strings of keywords that the VAs could copy and paste into the search bars on all those different sites. The entire process was automated. Then we would upload these lists into tools like ToutApp, which is now similar to Outreach and SalesLoft, and get emails going out and put everybody on a cadence – before cadence software existed. ToutApp didn’t have that functionality, and these other companies didn’t exist back then. So we had to kind of create this from scratch.

How to hire better for sales

Adam: Let’s fast forward to today. You’re advising more than 50 companies right now. They’ve made their first few sales hires, and they’re starting to scale their team. What are the biggest areas where they’re struggling? Is it getting their stack right? Is it transitioning from inbound to outbound sales? Learning how automation can supplement some of their tasks?

Max: For the most part, it’s outbound efficiency. There’s a handful of companies I advise where it’s transactional: it’s order taking. For everyone else, it’s the outbound sales process – figuring out the efficiencies, figuring out how to leverage your contacts to get referrals, figuring out how to break into enterprise accounts. A lot of the companies I advise are selling to mid-market and above, and that’s where my value is. There’s not really a lot of SMB, which is more like growth hacking rather than breaking into bigger deals.

A lot of my advising is actually around hiring. I have my network and I also can help vet some of the hires that these product and technical founders don’t really know how to vet. It’s about getting the right people, getting them onboarded, getting set up when they have no help, and then getting them to work.

For example, you’ll have a company that sells CFO software, and they want to hire someone with relevant experience, so what do you do? You hire someone who has a CFO and SaaS background. But if you’re a sales rep at one of those companies and you’re now going to a startup, that’s a huge jump. You don’t have a sales enablement person anymore, you don’t have a sales ops team, you don’t have a $10 million events budget or a $50 million demand generation budget. It’s a completely different experience. You’re used to getting fed leads, and now you have to go out and knock on doors and you don’t have a logo behind you. That’s the hardest part: setting up a process for a product founder who doesn’t know much about sales but wants to hire people who have relevant experience. Those people are all at bigger companies and don’t know how to sell at a startup. It’s a fundamental issue at the very beginning of almost all of these companies. A lot of the founders I work with are technical founders. They’re very good, but they don’t understand the other side of that business.

Adam: What are some of the softer skills that show a candidate from a larger enterprise would fit in in a startup sales environment?

If you’re a sales rep at a large company and you’re now going to a startup, that’s a huge jump.

Max: Well, the hiring process is their sales process. I like to see how they’re going about getting the job, how they’re having those conversations, how they get in touch. Do they back channel? What were some of the things that they did to get in touch with the company? What are some of the things that they’re doing to get the job? And I obviously ask them certain questions: “Pitch me your current product. How are you currently going out and seeking new business? Are you doing outbound? If you’re doing outbound, what are the things that you’re doing in that outbound process right now?” I can gauge if they’re being coddled at their current company and if it’s just an easy role, or if they actually do have to go out there and hunt because they’re not getting fed leads and they don’t have all these shiny pieces of software or collateral that’s helping them that earlier stage startups can’t afford. I think the actual hiring process is the best you’re ever going to see of the person you’re interviewing, so that’s kind of a sales process right there.

When we hired our last salesperson at Sales Hacker, it came down to two people. When I looked back at the beginning, one got in touch with us through a VP who I respect big time, and then the other one found all of our information and ended up calling one of the old sales reps and just asking how he should go about getting the job. If I’m going to hire a salesperson, that’s what I want them doing for me. I really liked how they went about it.

Adam: I imagine you learn a lot, too, from the types of questions they ask about how to qualify the right types of people, which is so important in those early days.

Max: You also want to make sure they have a good understanding of the product. They need to be passionate about the problem the product is solving. That’s so underrated in a hiring process. A lot of software is unsexy and boring, and if salespeople aren’t passionate about it, it’s hard for them to do a really good job at selling it. I have some product founders who are building really unsexy products in big markets, and they’re super passionate about it. You want them to be able to get their passion across to the person on the other side, but you can’t scale that. That doesn’t scale outside of the founders, so you need to hope that you can hire salespeople who really have a passion for that problem.

Maybe you’re hiring for a financial software product: you’re looking for a person who has a finance degree, came out of school and ended up somewhere like PWC for a year and then realized he wanted to get into sales. So he or she gets into sales, starting out selling stuff in the finance space. That person now understands the plight a little bit more and maybe has some passion about that product. What I like about Sales Hacker is that we help salespeople. When I hire salespeople, they are our audience. It makes it a little easier for us because I know that they understand our audience.

Cold calling is still a skill

Adam: One old-school skill you still find very valuable for salespeople is cold calling, because it makes you uncomfortable and puts you out there a little bit. Salespeople might have to do some of that today, but more frequently they’re doing things like writing outbound email, or they’re having inbound conversations inside of a messenger. How do you feel like those old-school skills translate to a lot of the new technology?

Max: What I love about cold calling is that if you can do that, you can do anything. That’s absolutely the hardest thing to do in terms of reaching a customer in sales. If you can hone that skill, then everything else will come easy after that.

I’m not sure that cold calling will exist in a decade, because we’re getting into a more text-heavy communications world, or at least a less reactive space. When we want something, we go out and do it, and then we’re on to the next thing. You see with products like Intercom, somebody will come to the site and they want information now. They have the 15 minutes and they’re on your site to get that information. Once they’re out, they’re on to the next thing. If you can catch them at that time, you have a much higher chance of getting to the actual meat of the call. It’s going to be so much harder to get a discovery call if you’re cold-calling or filling out a lead form or sending an email. If the person has their attention on your site right now, it’s very easy for you to qualify them there and set up the demo (not the discovery) and the next step of the process. It actually saves a lot of time on the front end.

Putting career advice on paper

Adam: Your newest book is called Career Hacking for Millennials, which is your newest book. You’ve also got a podcast with it. What’s the void are you hoping to fill with this project?

Max: This is a passion project for me. Last summer, LinkedIn changed their algorithm and started to make the newsfeed more interesting. I was posting these little quips about key learnings from my career. I didn’t think much of it, but they were getting thousands of likes and comments and hundreds of thousands of views. After doing this for about two months, I pasted them all into a Google Doc and had more than 10,000 words. I thought, “Wow, this is like a third of a book. I’m going to finish this up. I’m going to keep adding to it, and then I’ll have a book of just quick hitters.”

I read a book called Remote, by the founders of Basecamp, and it was just one- or two-page sections on how to build a remote team. I wanted to set mine up like that: here are the things to do when you’re building your career. It would have one page on optimizing your LinkedIn profile, and on the next page it’s how to not be so short sighted and tips on how to think long-term. The book is just my gift to other Millennials who are kind of lost, maybe where I was three, four, five years ago. Hopefully it will live on for a long time, because when you’re 20 years old, you’re thinking:“I have to graduate college in a year or two. Then what?” Then you get out of college and you get started on your career, and two years later you realize you don’t really like it. Then, maybe you switch and you try a different profession or a different path. People live their lives and then look back and think, where did the last three to five years go?

I happen to be very self-reflective. I free-write, and I journal, and I do some things to help me see how I’ve grown. Every Monday, I make a list of how I grew in the past week: things that happened the week before, what I’m stressed about, and what I’m grateful for. When I write that list, I see those incremental weekly gains I’m having as a human and in my career, and that’s important. That’s empowering, because you might go two years in your career think you haven’t done much. But if you had those notes from week to week, you’d see how much you were actually learning, and it would give you that extra push.

In terms of stress, when you put things down on paper, you can take the emotion out of them, and then it’s just a task. It’s a quick chart: “Can I do anything about this?” If yes, do it. If no, then you just move on. “Am I going to be mad about this in seven days?” If no, don’t be mad about it now, because it’s not going to matter in the long term. If yes, is it a month? Is it a year? Is it forever? So the stress thing just helps you lay it out and then realize that you really don’t have that much to be stressed about. It’s not as bad as you thought it was. Practicing gratefulness also helps too. I do this every Monday morning, so it helps start your week off on a good note. It’s like: “Hey, do you have food and clean water and a roof over your head? That’s a good start. Is your family happy and healthy? Do you have friends? Do you have dogs? Are you going on a trip sometime soon? Do you have a job?” These are all things you just make sure you write down each week, because you never know what’s going to happen.

Adam: Where can our listeners go to keep up with you and get their copies of both books we’ve talked about today?

Max: Career Hacking for Millennials and Hacking Sales are both on Amazon. I’ve got an awesome newsletter at getcareerhacking.com that features the six things that I’m really enjoying right now (a book, a quote, what I’m watching, what I’m listening to, a product that I just got, something new I’m trying, etc.) I also have a Career Hacking podcast, where I interview other Millennials or people who had interesting career arcs. I just interviewed the CEO of Hint Water, who was in business development for AOL and then just decided one day she was going to start an unsweetened but flavored water company, and now she’s doing all sorts of non toxic products. She’s really cool. Chris Voss, who wrote the book Never Split the Difference, did a session on how to negotiate when you have no leverage. Then saleshacker.com is obviously the resource for B2B salespeople.