Much of our work in the startup community revolves around pain points. We dig deep into a problem hoping to uncover its true source and figure out a resolution. If we’re lucky, we can create a product that solves the issue point-blank. But, even the best software requires a decent amount of upkeep. It’s a mentality Customer Success Managers know well.

CSMs spend much of their time getting to the root of a problem. The better they understand a customer’s pain points, the easier the conversation will be. …


At the core of every great work culture lies respect. I’ve worked with every type of business-from early-stage startups to huge global organizations-and witnessed it first-hand. The best run (and ultimately, most successful) companies foster a culture of respect and compassion for teammates, regardless of size or industry.

When we respect our teammates’ time, work, and intelligence, we can all reduce stress and stave off burnout in the workplace. The problem is that we’re all too quick to assume we’re already doing this.

We rely too heavily on the golden rule: Treat others how you want to be treated. But…


I’ve been gathering stories from Customer Success Managers as part of my ongoing learning for UpdateAI. One introduction led to another and I found myself speaking with dozens of powerful women leading CS teams.

UpdateAI Real Talk: CS + Parenthood

I quickly learned their pain points extended beyond the workplace. Especially this past year, they expressed feelings of burnout and anxiety. But this wasn’t a new feeling for most women in tech.

Too many working mothers have been forced to choose between their job or their children. And it’s not by their own doing. …


Managing a powerhouse Customer Success team requires a delicate balance of grit and empathy that most employees (and, honestly, most people) lack. We take for granted CSMs ability to bond with customers while pushing forward a sale. In the SaaS world, we’re so focused on tools and workflows that we often fail to see how mindset, confidence, and awareness impact the team.

We hosted a panel on Customer Success and Motherhood last month. It opened my eyes to some of the more intangible pain points managers face. …


Illustrations by Soyasama

If anyone from Clarisonic is listening, please help. I purchased your Rolls-Royce of face brushes nearly 3 years ago. It worked great. And then it didn’t. I’m pretty sure my warranty has expired. But maybe not. Who knows. Next time I’m buying a pack of washcloths.

Cue Woodrow Levin, Rohan Shah, Joe Moss, and Michael Darmousseh, founders of Extend.com, an end-to-end digitally native solution that eases the frictions of purchasing and redeeming warranties. They work with popular consumer brands such as Harman, JBL, Logitech, iRobot, SoClean, August Home, BlendJet, and more.

In less than 2 years, this founding team has…


Illustrations by @soyasama

Josh Schachter is an entrepreneur, product executive, and is Advisor-in-Chief of 1–800StartupAdvisor.com. John Tabis is Founder and Chairman of The Bouqs, a leading online floral delivery service.

After living on the West Coast for nearly a decade (a streak my mother would prefer ends soon), I’ve learned that if you can’t be there in person, send flowers! And that’s why since 2013, The Bouqs has been my saving grace. And the quality of the company’s product is quite impressive, as my family can attest.

At nearly the same time I was making my move to California, John Tabis was planning…


One of the most fascinating things about the role of the product manager is how resistant it is to definition. When talking to my family about my responsibilities, I often feel like Milton from the movie Office Space, answering to the two Bobs (in this case, my father and mother).

“Remind us again, what is it that you do?”

If defining the responsibilities of PMs is difficult, defining the value we deliver can be even more so. We know our value can be measured in specified step functions, yet even then the value can become a bit amorphous and shift…


(Author’s Note: Since first publishing this blog in October 2018, we’ve renamed the framework ‘The Startup Pyramid’)

Most of us have been, or aspire to be, operators of a startup. Operating a startup gives us a sense of autonomy, mastery, and purpose like no other professional track. Of course, we also know that operating a startup isn’t easy. We’ve all heard or experienced the cautionary tales of “blood, sweat, and tears” and the embrace of failure. We also know that success in operating a startup centers mainly around execution. Ideas are cheap, they say.

At BCG Digital Ventures, we recently…

Josh Schachter

CEO @ UpdateAI. Customer advocate. Builder of startup teams.

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