Your First Sales Hire Should be Senior

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One of the most important jobs for the Founder/CEO of an early stage startup is selling. We are talking to prospects, pitching the solution, gathering feedback, closing deals, and building the foundation of a sales process. When we start to see early success, our natural inclination is “This is working! Yes! If only we just could clone me so we could go faster…”

It’s at this point in the story where many founders make a critical mistake – a mistake I have personally made over and over again. We hire the “business hacker” – a hungry, ambitious, inexperienced person who we believe we can train in how to pitch, how to do cold outreach, and if they are good, scale from individual contributor to our future sales leader. We imagine that they will reduce our workload and enable us to sell more. Perhaps this person has some previous experience as a sales rep, but has never built a sales team or process from scratch themselves. Or, this person may have aspirations to be a founder – i.e., the “clone” that the CEO was hoping for.

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Taming Information Overload

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I used to think of myself as an information junkie. I read every news article I could find, endlessly scrolled through social media, and took pride in staying “informed.” While I may have been informed, I was not happy. Instead, I was stressed and distracted.

Many of us consume information reactively — we read whatever is put in front of us by news feeds, daily emails, social media posts or articles shared by friends. By default, we just absorb whatever information comes our way. The problem is, not all of that information is beneficial. In fact, much of it is totally unnecessary, and merely distracts us from focusing on more impactful things that would better ourselves and enable us to grow.

Last year, I made a conscious decision to exert greater control over the information I take in. It meant a major shift in mindset, from trying to consume as much information as possible to being heavily selective on what information I will benefit from. It has meant a disciplined approach to not read every article, not scroll through social media, not listen to every podcast a friend sends and ultimately, consume less.

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The Benefits of Routine

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I run every weekday morning at 7:30am. I run the same route, at the same time, every day. I don’t have to think much about it, nor do I agonize over whether or not today is a good day for a run. I just show up and go.

Routines are a remarkable thing. When they work, much of the mental load needed to make decisions simply melts away. Routines are the manifestation of systems created to achieve your goals. In his book Atomic Habits, James Clear writes “you do not rise to the level of your goals, you fall to the level of your systems.” Indeed, for many of us, establishing a system that creates a recurring routine is the best path to accomplishing a goal, whether it be staying in shape, writing in your blog or hitting your sales target.

Upon further reflection, I recognized many more examples of “routines” that help reduce mental load and ensure I am on top of my objectives as a startup leader. Here are the top 10 routines that I’ve found particularly beneficial:

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Interview Process for Senior Hires

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Effective founders and CEOs may spend as much as 50% of their time on recruiting. As the organization grows, most of the time gets spent hiring world-class functional leaders and other high-impact roles. The investment in time is usually worth it: when that “functional seat” is filled, the CEO can step out of the weeds and focus on the broader business.

Despite the heavy time investment, we often get it wrong. As much as 70% of new executives fail in the first 18 months. Making a bad senior hire is a costly mistake. A poor fit can permeate throughout an organization, contaminating everyone they collaborate with, spreading misaligned cultural values, taking the team in the wrong direction, or worse.

Therefore, it’s worth digging into the tactical process used to interview and assess a senior level hire. While there are many articles dedicated to great interview questions, sourcing, etc, I focused this one on the nitty-gritty steps through an interview funnel for a remote-first startup. Here’s the breakdown of how my team has done it at Crystal:

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Onboarding Remote Employees

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If you had told me in 2019 that in the following year I’d be hiring a VP Sales without ever meeting him in person, I would have burst out laughing.

Fast forward to 2020, and with the world in lockdown but business continuing, my team at Crystal doubled our headcount while operating completely remotely. Once the hires were made, we were left with the critical task of getting them up to speed and productive as fast as possible, all while working from home.

As I thought more about the task ahead, I recognized perhaps the most crucial difference between remote and in-person onboarding:

  • In person, when your new employee has a complex question, it’s really easy and socially acceptable for them to walk over and ask you.
  • Remotely, when your new employee has a complex question, they need to take the initiative to call you, or put the effort into wording it the right way in Slack.

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Multi-Functional Leadership

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The news hit me like a load of bricks:

Our VP of Sales and Customer Success were leaving the company.

At the time, my startup was going through the growing pains that many do, including turmoil amongst the leadership team. With this leadership transition, there was now an immediate gap that would need to be filled in order to keep the company operating smoothly.

I was serving as VP of Growth, overseeing marketing and operations. I had developed a reputation as someone who is willing to take on whatever is needed, and while I may not have been qualified to have the responsibility on Day 1, I was willing to quickly learn. So, it wasn’t a surprise that as the rest of the leadership team gathered, we decided that I should absorb those functions for the time being.

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Distractions Kill Startup Productivity

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There’s a common frustration with startup offices:

They are too loud.

Anyone who creates things — whether it be coding, designing, or writing — recognizes the benefit of deep work. The term was popularized in a book by Cal Newport, and the premise is straight-forward: in order to complete a cognitively demanding task, you need to focus without distraction. While this concept has been called many things, such as “hitting flow” or “being in the zone” it basically means that if you want to get shit done, you have to focus on it.

Your professional future usually depends on your ability to get shit done, and that’s a problem, because many startups are inflicted by a plague that has crept up among the ping pong tables, open floor layouts and endless chat conversations. That plague is noise and distraction, and it can kill productivity. When I say noise, I don’t just mean physical noise of people talking loudly in the office (though that is certainly part of the problem), but I also mean digital noise, from Slack channels and email threads that suck away our attention into conversations that we often have no need to participate in.

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How Startups Should Manage Costs

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There’s a problem at many startups:

We spend too much money.

With the decade long bull market and excessive fundraising environment, unprofitable startups are gobbling cash at a remarkable pace. The mantra is “grow as fast as possible, raise the valuation, figure out profitability later.” That can certainly work for some, unless the music stops. If there are unforeseen circumstances — a new product doesn’t work or the business model shows some flaws — that spigot of never ending money may stop flowing.

I felt this pain acutely at my last startup. We grew quickly and let hefty expenses, many for products and services that we didn’t even need, pile up. Our leadership team was eager to add more staff to scale, but we didn’t carefully consider how the additional costs would reduce our runway and increase our risk, especially if revenue did not grow as quickly as we projected, or if we couldn’t collect accounts receivables promptly. Not surprisingly, we encountered both of those obstacles. This forced us to make layoffs, which is agonizing for everyone involved. It was a valuable lesson learned and shaped my current philosophy on cost management.

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The Product Funnel

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This article is the 1st in a series about startup product and engineering.

If you’re building a software company, one of the most important things to get right is… (drum roll)… building software. Yet building good software is among the most challenging parts of a tech startup. Most founders can hack together a minimum viable prototype that gets the job done for early customers. However, as more customers use it, that prototype typically breaks and becomes difficult to maintain. Therefore, it’s critical for startups to hire a great team of engineers and product managers to make that prototype scale.

Growing, organizing and managing a product and engineering team brings an entirely new set of challenges. The costs of getting it wrong are staggering: software bugs, instability and perhaps most acutely painful, not being able to quickly iterate on your product to get to product market fit.

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The Ultimate Bootstrapped B2B Marketing Stack

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Suppose you are in the early stages of launching a B2B startup. You have a minimum viable product ready for the world to use. You then realize, “oh crap, now we actually need users/customers, I better figure out marketing…”

The most difficult part of getting off the ground is often not building the product or even getting customers to pay. Instead, it is the fundamentals of marketing: driving traffic to your website and converting visitors into users.

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