What You Learn at a Startup that Grows from $0 to $7.75 Billion in 2 Years | by Dave Schools | Sep, 2021

Everyone has imposter syndrome.

“If you haven’t done something at least three times successfully, don’t assume you know how to do it successfully.” — Ray Dalio

There’s a lot of insecurity when you’re doing something you’ve never done before. Many times at Hopin, I didn’t know what I was doing. The vast majority of startups take over 10 years to reach $100 million ARR, but Hopin is breaking records. I’ve never run marketing at a hyperscale remote startup before. There’s a type of panic that sets in just before a meeting when you know your best answer, despite how deeply you care and desire to help, isn’t going to be good enough.

But I wasn’t alone. No one had experienced this type of rapid growth before. Hopin was different. For everyone. When you realize everyone else is neck-deep in imposter syndrome just like you, it’s mildly reassuring. What matters is that you keep learning, keep driving, keep experimenting, and keep solving problems wherever you are. Constantly ask yourself the question, “What am I not seeing?” to try to stretch your thinking. See section “How to be strategic.”

Avoid “old-timer syndrome”

I stumbled upon an article Elad Gil wrote called Old-timer syndrome & early employees and I immediately felt like I had met an old childhood friend who knew me better than anyone else. In the article, Gil discusses the opportunities and pitfalls of being an early startup employee, highlighting what helps make early employees scale and succeed or stagnate and fail. Two of the best quotes from the article were:

1. A common sign that an old-timer will work out is their eventual acceptance that their role and influence at the company will shrink in the short- to medium-term as the team scales, but that it will expand with time as they continue to learn and the company continues to scale.

My best skill is probably my willingness to take action even if it means I might be wrong. So much of the early days in a startup is experimentation and experiments often fail. One of my life quotes is “teachers teach, coaches coach, entrepreneurs fail. It’s part of the job.” Many people desire to “be right” in what they say and do but when you work in an environment where there are no right answers, you need to be able to operate while surrounded by unknowns, and be ready to accept and adapt quickly when you learn a better way.

2. Early employees who are humble enough to realize they can learn from fresh blood can grow with the company.

Hopin has so many incredibly smart people. It makes utterly no sense to me to be defensive and try to retain control of “what’s mine.” Elad Gil observes that self-protection is the enemy of growth. Rigidity is the number one way to fail as an early startup employee. The sooner you can learn to let go, the sooner you can help grow the company and grow as a professional.

I highly recommend reading the interview with Ruchi Sanghvi, early employee at Facebook and Dropbox, from Elad Gil’s book High Growth Handbook.

Roadmap marketing.

Something I learned from Johnny in the early days about B2b software sales was this idea of “roadmap marketing.” At Hopin, if Johnny was on the call, we never lost the sale. The reason was, if a prospect on a demo asked about a feature we didn’t have, Johnny would ask when their event was. They’d answer with a date. Johnny would think it over for a moment. Then answer, “Yes, we’ll have it by then.” He knew we could build it by then, even if it meant he himself jumped into the code. If they signed, that date became the new deadline to ship the requested feature. And we always did. The takeaway is don’t be afraid to sell a feature that isn’t quite in production yet. Sell the roadmap. Not only does it light a fire under the whole company to delight a client by delivering by a deadline, it also is highly probable that by the time it’s shipped you’ll have just gotten through legal and procurement.

Think in deliverables.

This is simply a startup-y way of restating Steven Covey’s principle “Begin with the end in mind.” The key to early-stage rapid growth is to not just think and talk about ideas but to attach everything you spend your time on to its external impact on the customer and on revenue. Don’t waste time with grand plans and six-month strategy decks at this stage — they’ll need to be updated or thrown out completely as changes happen rapidly and it’s impossible to predict anything beyond a quarter. If you’re doubting that previous statement then you’re not experiencing early-stage hyperscaling. It’s a tough spot to be in because you need to be thinking two steps ahead while always delivering on the now.

“Be like water.”

Adaptability and flexibility are key to hyperscaling. “Be like water” was a common management mantra at Hopin used to remind the company to stay agile, embrace change, roll with the bumps, don’t take yourself too seriously, and be ready for any curveball the market might throw at us.

Move at Hopin Speed

In the early days, speed wins. Hopin became known for shipping features fast. Almost every week we would release a capability just in time for a big event to showcase it. This speed and responsiveness helped us bring in whales and beat out the competition. However, there were always key learnings to improve upon and as we started hosting our own events with over 10,000 registrants, the stakes became even higher. Quality was also massively important and we evolved to emphasize both speed and quality for our long-term strategy and customer success.

Speed and quality tend to be at odds with each other. Every startup needs to balance both but also needs to decide which one they’re optimizing for. Knowing when to shift focus can be a difficult choice.

Acquisitions are the ultimate test of adaptability, clear communication, and trust-building.

Hopin has acquired five companies: StreamYard, Streamable, Jamm, Attendify, and Boomset. Of the many lessons to learn from when two companies get strategically blended together, I’ve learned that it’s important for the acquiring company to not come in with guns a-blazing. You’re not coming in as a superior but as a supporter. The acquired company is often killing it in their space already. Don’t disrupt the good that’s currently going on. Instead, become a student. Learn what’s working and what’s not and even when you see inefficiencies, resist the temptation to give orders. It takes more than a few meetings to understand what’s really going on. Do an extended listening tour. There’s no need to prove anything. Simply take the time to build trust. It will be worth it in the long run.

Don’t just ask for feedback, make space for it.

As managers, feedback won’t happen unless you ask for it. It also won’t happen unless you free up the calendar space for it. Being back to back all day every day sends the message that you’re too busy to talk through something. See section: “Good managers vs. bad managers in 1:1s.”

Creating a GTM and marketing org structure

I have learned more lessons from Armando Mann and also Anthony Kennada, Hopin’s CMO, than I could list here. One main lesson both of these leaders have shown me in their own way is how to structure an organization. From Armando — I saw how to build a SaaS GTM org from the ground up: Sales (AEs, SDRs, BDRs), Marketing, Customer Success, Support, and Biz Ops. From Anthony — how to structure a scalable SaaS marketing org with four pillars: Brand Marketing, Product Marketing, Revenue Marketing, Corporate Marketing. It might sound like something you can google but it’s not. Every company is unique and nuanced. Seeing Armando and AK wrestle with problems, think strategically, and bring the right people in at Hopin has felt like a hands-on double MBA for me. I’m grateful.

The question that cuts right to the true north metrics

Armando showed me an interesting insight about managing and metrics. Several times, I’ve been in a meeting where someone reports on their metrics and Armando will kindly interrupt and ask something to the effect of, “But what is the number you care most about and why.” He asks them what is the true north they’re optimizing for. He wants to know why it is important to them. It’s such a clarifying and focusing question. By asking it, it cuts out the surface level cruft numbers and vanity metrics and goes right to the person’s core operating strategy and how they measure it.

The early-stage hiring pickle

My biggest fault at Hopin was not hiring fast enough. I hired seven people on the marketing team when it should have been triple that. One of the reasons why I was slow in hiring was I didn’t realize how much time high-quality hiring takes. As a marketing team of one supporting a GTM team of hundreds while also managing a dozen agencies, I didn’t have a lot of time in between responding to fires. This is the early stage hiring pickle. The time it takes to hire right is time not spent on strategy and execution. But part of the solution is to slow down in order to hurry up. It might mean temporarily disappointing a teammate or two, but it’s critical to invest in getting your first few marketing hires right.

Good managers vs. bad managers in 1:1s

I’ve learned that weekly 1:1s are actually the place where professional management skills happen the most. 1:1s are where good managers and bad managers are revealed.

A good manager is generous. They listen, genuinely curious about how their direct reports are doing inside and outside of work. They reflect, coach, unblock, and share helpful context. They regularly ask permission to give feedback. They deliver feedback with clarity and objectivity. They do anything to make their direct report more successful and happier with their job.

Bad managers are defensive. Instead of listening, they have a list of tactics for you to do. They never ask for feedback. Or permission. They’re too vague and dodgy when they give feedback, if they give it at all. They don’t make time on their calendars for you. They make problems bigger than they need to be. They make problems personal. They only hire people they can control. They buck against process. Cowboys aren’t good managers.

How to manage people you disagree with in Slack

When you disagree with someone in Slack, or need someone to take a new direction, I’ve seen that the best managers at Hopin do not write a message like “Don’t do that, do this” — which can come across as authoritarian, pushy, and bossy and thereby disempower or disenfranchise the individual. They write a question instead.

The question is phrased strategically as a yes or no question but the answer will be far from a yes or no. It might seem counterintuitive to ask a closed-ended question instead of an open-ended one, but it gets right to the core issue and directs them to take an action.

Some examples might be, “Did you factor in Jonah’s research analysis here?” “Is our Google Analytics traffic in line with this conclusion?” “Has this been AB tested?”

If they respond yes, great, they’ve thought about it and it might mean you need to reexamine your disagreement or reframe your question to something you know they haven’t thought about.

If the answer is no, what will most likely happen is now that you’ve asked the question, they will think about it, and instead of answering no, they respond with a plan or action in the direction you were looking for.

The most common reason why someone gets hired over is because they weren’t “strategic” enough. I’m guilty of this. Both on the receiving end and the giving end.

Being strategic is a direct indication of how big you’re thinking. Fast-moving companies need articulate big thinkers. Thinking big means seeing the big picture, setting the right goals, and envisioning not only the desired state of the future but also the KPIs, systems and processes and team it takes to achieve it. Thinking small looks like just a list of KPIs. It looks like achievable and predictable goals. It looks like a document or deck that is unclear, unstructured, and hard to follow.

Your strategy is a reflection of your experience. Some quotes say that experience doesn’t matter. That’s baloney. When you’re at a fast growth company and you’re responsible for creating a strategy to lead your organization, you fall back on your experience. If you’ve never done it before, it will show. Billionaire Ray Dalio has a principle: “If you haven’t done something at least three times successfully, don’t assume you know how to do it successfully.”

Sure, you can find the mentors, data, templates, and tips from places like Twitter to help put something together, but how you communicate it, how you walk stakeholders through the deck will reveal your confidence. Your experience really comes through when it’s questioned — does it stand up to scrutinizing inquiries? Is it connected to a vision anchored in reality, or is it just a pretty looking document with well-written concepts?

The sign of a good strategic thinker is not that they have just articulated the problems, goals, plans, people, and metrics of the next quarter. That’s table stakes. They also have the story, the narrative, that they’re creating. They can confidently describe what the future looks like. And it often looks like a version of something they’ve experienced in the past or from history or from another player in the market that they’ve studied. They have a model they’re building off of.

Once you have the story, the last part of being an effective strategic thinker is the ability to communicate it and gain internal traction and 360 buy-in.

Authenticity isn’t polished.

In February 2021, we hosted an event called Hybrid Unlocked. With over 11,000 people registered, Hybrid Unlocked was a grand experiment. The content sought to explore the emerging frontier of hybrid events. The program alternated between formats of live video and semi-live video (prerecorded video that is streamed live).

Interestingly, the prerecorded content didn’t resonate with the audience as well as the live content. When viewers realized the prerecorded content wasn’t live, they began criticizing the content in the chat. But during the live content, such as the panel, the audience was more involved in the discussion, asking questions and responding to points in the chat.

The observation is that polished, scripted, and produced video isn’t always better than off-the-cuff, unedited live video. Often, the benefit of live streaming is a more genuine and authentic feel.

This doesn’t mean preparation isn’t important. Rather, it means “content quality trumps production quality,” said VidYard VP Marketing Tyler Lessard on Finite Podcast. GaryVee is a good example of this.

Take advantage of live streaming. Brands including Salesforce, Atlassian, Peloton, the NY Jets, and more use StreamYard to connect with their users and share authentic stories with their communities.

I’ll end with one that goes back to the beginning. A number of factors led to me meeting Johnny. One of them was, and this is subtle, if you look back at the intro email to Johnny: the “interesting app” I was working on. Party Qs was a side project, and was enough of a reason for the interviewee to shoot off an introduction email to Johnny. Common advice says that opportunities like this come from networking and saying the right thing to the right people at the right time, but to put it into more of a concrete takeaway, I’d put it like this:

Always have a project that puts you out there. A project that puts you out there could be anything — an app, a website, a blog, a product, a consulting service, a book, a side project, a hobby, a community, an event. As long as you’re consistently working on it and therefore being seen and meeting new people, it’s just a matter of time before you get lucky.


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