5 min read

What do 20 of Boston’s Top CEOs Want to Talk About?

Pictured above from left: Ellen Rubin (CEO, ClearSky Data), Matt Johnston (CEO, Mautic), Jamus Driscoll (CEO, Salsify)

3 insights from startup to multi-hundred million dollar business leaders.

The Underscore Core Community is a curated group of Boston’s top founders and operators that inspire us to invest and build great companies together.

You may wonder what on earth 20+ CEOs would sit down at a dinner table and talk about. It was a privilege to be able to listen and learn from them, and I’m happy share three of the topics and some insights with those who weren’t able to make it.

Going Global

As startups grow, many executive teams begin to think about how best to expand their development base offshore to scale. There are many factors that go into deciding on the right city, here are some that the Core Community shared.

Convenience or Culture?

When hiring overseas, much more goes into decision-making than where team members would be excited to visit. CEOs must consider talent pools, productivity rates, time zones, and convenience of access with direct flights, with an eye on the future to expanding a location as a broader GTM and international hub. As Salsify looked to expand their development team offshore, all of these things were on their minds.

How early is too early?

“It has to do with the relative maturity of your product or organization,” Bryan House, Chief Commercial Officer of Neuralmagic, remarked.

When companies are trying to gain their footing, determine their product/market fit, and build something tangible for customers, it’s not the best time to distribute their team. Ellen Rubin, CEO at ClearSky Data, voiced that in early stages, it’s especially important for engineering teams to stay close to the customer.

If you’re going to distribute, invest in the tech.

Technology in the workplace has grown leaps and bounds, enabling organizations to have a more flexible work culture that allows them to easily collaborate. But how do they overcome barriers of communication that come with remote employees? The simple answer is to invest in always on, instant access videoconferencing technology (click to tweet). The consensus was quality over cost.

Services like Zoom and cameras like Owl Labs came up in the conversation as top choices for startups that allow remote team members to get up close and connected to the rest of the team. Some even had success with robot presence iPads. Don’t laugh — sometimes you need physical ability to approach and tag a fellow remote team mate!

Determining Pricing Models

As you can imagine, pricing can be considered a science and an art. Many anecdotes showed that there are at least some basic frameworks to apply when approaching this. Jamus Driscoll, CEO at Moltin and former Demandware executive offered his insights on how Demandware determined their pricing model.

From left: Jamus Driscoll (CEO, Moltin) and Jason Purcell (CEO, Salsify)

“Demandware initially was pricing by pageviews, and many other things, and those metrics weren’t getting close enough to what customers valued most. We spent time trying to understand what customers wanted, and what they really cared about was growth, that their website was going to run, that they could predict what the expense was going to be, and how much they were going to pay for that peace of mind.”

— Jamus Driscoll, CEO, Moltin

Jamus’ statement highlighted one of a few other points made below.

  • Do lots of A/B testing, on a deal by deal basis
  • Use MVS (Minimum Viable Segments) to pick segments to test, rather than being random
  • Deciding on the right unit of measure that the survives the test of scaling
  • Ensure the customer’s value metrics are proven to them during the use of product. (ROI may come later but breakthrough value or what was not possible before and is now should be clearly visible)
  • Create a paradigm-shift in pricing that beats out competitors (EG Demandware’s shared customer success pricing)
  • Aligning with the sense of emotional connection — ultimately people buy from people and emotion is a key factor

The value metrics need to be evident to the customer and obvious for each decision-making unit to champion internally. You can’t price something that people can’t understand or are unable to prove value from. Pricing is a key element of the business model and can be apart of changing the game and establishes a competitive advantage (click to tweet). One of the fearless founders in the room, whose identity we’ll keep private, uses the squeal test. His take on pricing models is simple:

“It still comes down to how hard the customer squeals.”

As you can imagine, a fun debate ensued on how to balance value appeal and squeal!

The Impact of Slack Culture

Communication is the lifeline of every startup

In recent years Slack has revolutionized the way teams interact with each other and for some like Erik Peterson and the CloudZero team, messaging systems like Slack have almost completely eliminated emails.

“99.9% of the email I receive comes from outside the company. Nobody sends email internally.” — Erik Peterson, CEO, CloudZero

When asked for a show of hands on how many companies primarily use Slack, every single person raised their hand. This communication tool has made significant waves. What stuck out most, however, was how companies are utilizing it for customer insights.

In early stages it’s especially important to understand what kind of product needs to be built. Slack has made it so that startups can create channels with each of their customers in order to facilitate immediate feedback, send prototypes of new designs, and personalize the relationship further (click to tweet). The CloudZero team has seen tremendous results with these methods.

“Whenever we have a new design we want to try out, we just copy it into the individual Slack channels that we have with customers,” continued Erik.

Erik Peterson (CEO, CloudZero)

Though Slack has proven to have a significant impact on organizational communication, it still has its problems, including having too many channels. Many large companies have an Exchange admin, but in this day and age, might we need to implement a Slack admin. Time will tell.

Finally some remarked that, like the move from email to text, expectations get set and with Slack usage it likewise creates pressure to respond.

“The most overwhelming part of Slack is people feeling like they need to respond immediately. Once that starts happening, Slack will become more of a weapon.”

— Erik Peterson, CEO, CloudZero

If you are a startup or growth CEO share what you’d like to discuss. If you were a CEO what would you like to discuss? We look forward to hearing your thoughts in the comments.