How to run a team offsite

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Remote work brings many efficiencies, from eliminating commutes for employees to reducing real estate costs for organizations. However, having a remote workforce makes the times that the team gathers in person all the more important. Team offsites – dedicated, extended period of times where a team gathers outside of the office – may be the only time that remote employees engage in real life, and are prime opportunities for planning, reflecting, and bonding. Offsites are a big investment in both time and money… every team member is not only potentially traveling on planes, but also taking a break from their day-to-day tasks to participate in the offsite. Considering these costs, it’s important the team leaders put significant thought and planning into an offsite in order to get the most value out of it. 

Given this is such an important topic, I enlisted the help of my friend Kirsten Newbold-Knipp, a GTM exec who has led sales and marketing teams of 5-50 people at companies like FullStory, HubSpot and Bigcommerce. Our thinking is aligned on the value of offsites and I’ve included some of her best practices in this discussion.

The last several leadership teams I have been a part of operated remotely, and we developed best practices to make our offsites effective. This article is a tactical playbook to help you run a great team offsite. While the examples are often referencing startups and scaleups, many of the insights are applicable for division offsites at larger organizations as well.

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Start Marketing Before Sales

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It is amazing how much traction a business can get on purely founder-led and word-of-mouth sales. Many companies go years, and reach significant milestones, before building a sales team, and those with product-led growth can go even longer. However, the “no sales team” approach often has a ceiling. At some point, growth may start to slow and flatten. Typically, the desire to build a sales team increases as a business wants to move up-market towards larger customers that bring more significant and secure revenue.

When that time comes, the company is ready to build a true go-to-market (GTM) motion powered by sales and marketing. This is where many entrepreneurs and operators make a common but critical mistake: we try to start doing sales before we have marketing.

At first glance, it often appears that we can “brute force” the sales process by hiring an individual, high-performing sales rep and just hitting the phones or cold emails. While this can yield some results, it is often a fool’s errand because that sales rep lacks the marketing and sales management support needed to be successful. So, why is it so tough to make sales work prior to having any marketing in place?

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Amp It Up: My Favorite Book of 2022

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Frank Slootman may be one of the most effective tech CEOs of all time. He has written several books about his no-nonsense operating style, from growing Data Domain from tiny startup to billion dollar acquisition in the early aughts, to now leading Snowflake which had the largest software IPO ever in 2020. It’s no secret among my friends how much I admire Frank’s approach; in fact, some have started referring to me as “Sklootman” – a comical nod to our similar names.

Frank’s most recent book, Amp It Up, tells the story of his career and offers a plethora of guidance for anyone who is operating a growing business today. You can buy the book here, and below are my top takeaways and quotes.

1. Clearly define a priority

“Priority should ideally only be used as a singular word. The moment you have many priorities, you actually have none.”

As with much of what Frank writes, it’s so simple, yet rarely executed well. We cannot prioritize when everything is a priority. This plagues so many organizations, from chasing the random whim of the CEO to overreacting to market news and quickly pivoting a strategy. The best run companies have a very small amount of clear priorities, and ruthlessly focus on executing them well, pushing everything else aside.

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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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