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How to Lead in an Early-Stage Company with Eric Hann (Order)

How to Lead in an Early-Stage Company with Eric Hann

There’s no single playbook that works for every startup. But one thing they all have in common is a strong foundational team. 

If you have the right team, it’s easier to set your business up for success. 

Eric Hann is an expert at helping early-stage companies find their go-to-market fit. As the Senior Director of Marketing at Order, Eric has learned what makes a startup team great—and what to avoid. 

In this episode, Eric shares how to build a demand generation team and program from scratch, why you need curious team members, and how to lower your employees’ fears of failure.

Show Topics

  • Create an environment that doesn’t fear failure
  • Stay grounded in what’s repeatable
  • Learn the rules of the game
  • Build your startup around curious people
  • Hire people who ask questions
  • Be a generalist
  • Follow a situational leadership model
  • De-risk new challenges
  • Evaluate your processes
  • Make your own experiences

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Key Takeaways

12:06 – Create an environment that doesn’t fear failure

Startups are a great place to fail as you try new things because you don’t have the same pressures at a startup that you have at a larger company.

“When you’re at a startup, usually the fear isn’t, ‘I’m going to break something.’ Automatically, just by nature of being the first to build something, it really engenders the mindset that it’s okay if I fail, because that’s the only way I can turn it into something that’s valuable. Sure, for a company, but also marketing programs. So, if you’re coming into a really established company, you might be worried, ‘Oh, if I send a bad email, it’s going to be the end of the world.’ And there probably is real revenue tradeoffs at a large company if that happens. But at a startup, you don’t have an audience yet, so you’ve got to figure out how to build one. So, therefore you can do stuff that is a little bit more wild west, as long as you’re disciplined and measuring and thoughtful in your hypotheses, it actually starts to work.”

15:04 – Stay grounded in what’s repeatable

In a startup, you have to support the sales team. This means you can’t be a hundred percent speculative—you have to be grounded in what’s repeatable. 

“One thing that’s interesting about the startup space is you have a very real need to support the sales team while you’re doing it. So, you can never be a hundred percent speculative in marketing tactics. You need to be somewhat grounded in what’s repeatable, and that usually costs a lot. So, often you’ll find you need either an agency or an in-house expert to have some paid mechanism that gives you the lead runway to start testing all those other speculative things as a balance. So, that’s what we did in different forms at Mainstay and in now at Order, it’s how do you build an engine that can supply what you’d expect from the sales funnel, just in terms of hitting your real demand goals while also starting to branch out into these other things, to see where you can get an audience.”

16:25 – Learn the rules of the game

Every company lives by different rules, so it’s important to figure out what those rules are and how best to follow them.

“You have to learn what are the rules of the game, and they’re different at every company. And those rules are usually dictated by your model, and your LTV to CAC, and how expensive your product is, and your conversion metrics. So, basically one of the first things to do if you’re trying to figure out how to spend money to drive demand, in my opinion, should be you find out how much can I actually spend for a conversion? And how do I know I can spend it? And how do I know as a cohort, if that’s good spend or not, or efficient spend or not? And that’s going to be different depending on where you work. If your software costs a thousand bucks or $10,000, that changes a lot. If you can target a large audience or very specific niche, then that also changes a lot. So, I think there’s a calibration phase of how well do we understand our ICP? What unit economics do we need to play within just to get lines on the field?”

31:04 – Build your startup around curious people

You need to build your startup around curious people because they are the ones who help you problem solve and refine your product.

“There’s a few things that I think are really required for success. The first one is an innate curiosity. If you’re in a world where you’re building and iterating by definition, people who have an innate sense of curiosity, who are going to ask 10 levels down worth of questions to figure it out. And I would say there are people who are oriented to searching for root cause. Those people do really well because each step will require that to get it to a place where all of a sudden you’re like, ‘Yeah, we should do this as much as you possibly can.’ I think a lot about the life cycle of a channel or a tactic as the first step is, ‘Is this even predictable? If we do it, can we tell you how much will happen?’ And then once you have predictability, then the next thing is, ‘Can we do it again?’ And then if you have repeatability, then you can start to be like, ‘Okay, how do I optimize and scale?’ And in order to get through that life cycle, you need someone who just innately, regardless of marketing background or anything else, can seek where things fell short and why.”

32:21 – Hire people who ask questions

When you’re interviewing potential candidates, hire people who ask good questions. They’re the ones you want on your team.

“One is what questions they ask me in interviews. I put a really strong bias on that. There are folks that you can tell in an interview that seek understanding based on what you said versus just ask a question and they go, ‘Okay.’ And then move on to the next question on their list. And I feel bad because some people are just nervous on their feet. So, maybe we’re screening people inappropriately in that sense. Well that’s not true. One person that did a really great job, they didn’t have good questions on their call, but then they send an email afterwards, having processed it. That’s a good way to see still curious, but more of a processor than a real-time conversation person. So, that’s one way. Another is you can ask questions like, ‘What have you learned recently?’ One from HubSpot that I always loved is, ‘What’s something that you’re an expert in? Or in a room of a thousand, what’s something you’re the best at?’ Because people who have a mechanism to get really good at something understand that it by nature takes failure and iteration.”

36:38 – Be a generalist 

Generalists tend to do really well at startups because they know how to jump in wherever they’re needed at the time.

“People who are comfortable being generalists tend to do well at startups because they can float and they’re comfortable with, I would say, shifting responsibilities. And a month in a startup feels like a quarter in other places. And that usually just means that the nature of your work might change a lot as you start to build those things. So, people who come excited to just try new things in general. And let’s say repetition might not be the most exciting thing for them. And they’d rather have the opportunity to try a lot of things and maybe have already done that successfully. They do well. And if that generalist also is an expert at something important, then they do very well. So, if there’s someone who can say, ‘Hey, firmly, I am world class at this, and I also like to try my hand on a lot of things with well-rounded skill sets.’ That’s who you want to stack your team on in a startup, because it gives you both bedrock to build programs with adaptability if the business requires it.”

43:18 – Follow a situational leadership model

Situational leadership is one of the best models to follow because your goal is to manage the skill, not the person.

“I think situational leadership is one of the best models that I personally think and try to implement, which is you manage to the skill, not the person. So there are people who are probably really good at something and you can just delegate that and be a support mechanism if needed. And then that same person probably has skills where you need to be really directive with how to do it the first time. And I think some managers make the mistake of just thinking of a person as senior, but really it’s this person is senior at certain things and they’re junior at other things and making sure that you’re thinking through that as a manager. Second is building the culture that engenders people being open about that without feeling like it jeopardizes their career path. Because if someone feels like if they admit they need to build a skill it would block their promotion, then they’ll never proactively seek the council to coach them on it in the first place. Psychological safety is a pretty trendy term. I just think of it as, do you lead with humility and vulnerability? And is that accepted on your team as something that’s expected?”

45:06 – De-risk new challenges

Give people a safe space to fail by de-risking new challenges. This allows people to improve over time without fear of repercussions.

“If there’s somebody who has to try something for the first time, you can de-risk it while also giving them space to fail and iterate on their own. One of the things that our team has that I think works really well is a retro mechanism where every two weeks we come together, we talk about what worked, what didn’t, how do I make it better? It’s expected that you reward the insight to make it better. It’s a hot Eric-take, but one of the drawbacks of the scientific community is you’re disproportionately rewarded for success, and failures you’re better off to not promote. And that just leads to a lot of waste. So, in a business setting for marketing teams, anytime you can amplify, honestly, failures through the context of we reduced a known unknown, that’s just the good of the team. And if you celebrate that as a leader, then all those people who are having trouble adopting that framework, you can use that as a mechanism to show, ‘Yes, we actually will reward people who show vulnerabilities.’”

56:42 – Evaluate your processes

Ask yourself: Is this process making my job easier or faster? If the answer to both of those questions is no, your process needs to change.

“The way you know a process is working is it accelerates. If you ask yourself, ‘By doing this process, is my job easier or faster?’ and the answer’s no, break it. Do something different, or remove it entirely. Lots of people want things to be in these clean tight boxes, especially if they’re really strong operators, but that’s not the right play for a lot of scenarios. So, any business where moving quickly is tantamount to success or learning, you need the minimum viable process to enable that to happen as quickly as possible, and maybe that’s a standup and that’s it. And maybe that’s an Asana board or an Airtable board or whatever, if that’s what works for you. And maybe it’s different for each team member. If the goal is move quickly and you’re in a scenario where you have to do that, sometimes peeling off some of those required things is better so long as you’ve hired the right people. And I think that’s the big part because actually this is a big part of that whole Netflix book, ‘No Rules Rules.’ If you’ve hired well, you can remove some of those constraints. But I think that’s especially true in any company that needs to move quickly by necessity.”

01:00:22 – Make your own experiences

When Eric didn’t get into a rotational program, he decided to create his own. If your career isn’t giving you the experience you need, go out and get it another way.

“I was pretty bummed I didn’t get into one of those canned rotational programs, which were a big deal back in the day. You get a cool, big company rotational program. I was speaking with somebody at the time, they’re like, ‘Just go make your own.’ And I was like, ‘What do you mean?’ He’s like, ‘Just go get a job in each of the things you want to do. You can do that and it doesn’t have to be here.’ It blew my mind. Because, especially at the time, I was really jazzed to be working, Liberty’s a great company. At the time it was a labor shortage. So, it was just a bad hiring market when we graduated. So, the concept that I could just go work in different capacities that ultimately served a career better, it didn’t feel like I was restarting a career four times. It changed it to, ‘No, I’m building four different skill sets in four different jobs so that I can get to the next thing that I want to do.’ Which was really impactful, and I did that.”

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David Khim

David is co-founder and CEO of Omniscient Digital. He previously served as head of growth at and Fishtown Analytics, and before that was growth product manager at HubSpot where he worked on new user acquisition initiatives to scale the product-led go-to-market.