Preparing For The Future Of Work: Matt Martin of Clockwise On The Top Five Trends To Watch In The Future Of Work

An Interview with Phil La Duke

Authority Magazine Editorial Staff
Authority Magazine
Published in
12 min readOct 27, 2021


Burnout boundaries. According to a survey from Deloitte, nearly 70% of professionals feel their employers are not doing enough to prevent or alleviate burnout. Every organization needs to have a plan for how they’re supporting their employees during a time like this. For example, many of the organizations that use Clockwise establish No Meeting Days and dedicated meeting hours to give people time to concentrate and avoid work from bleeding into nights and weekends.

There have been major disruptions in recent years that promise to change the very nature of work. From the ongoing shifts caused by the COVID19 pandemic, the impacts caused by automation, and other possible disruptions to the status quo, many wonder what the future holds in terms of employment. For example, a report by the McKinsey Global Institute that estimated automation will eliminate 73 million jobs by 2030.

To address this open question, we reached out to successful leaders in business, government, and labor, as well as thought leaders about the future of work to glean their insights and predictions on the future of work and the workplace.

As a part of this interview series called “Preparing For The Future Of Work”, we had the pleasure to interview Clockwise Co-Founder + CEO Matt Martin.

Matt Martin is the Co-Founder and CEO of Clockwise, the smart calendar company that’s reimagining the way people work. Clockwise is an intelligent calendar assistant that frees up your time so you can work on what matters, using artificial intelligence to understand your work and life commitments and automatically organize your calendar to help you focus on your priorities. Prior to starting Clockwise in 2016, with co-founders Gary Lerhaupt and Mike Grinolds, Martin was an engineer at RelateIQ, a relationship management software firm that was acquired by Salesforce. Matt earned a BA in government at Dartmouth College and JD from the University of Pennsylvania Law School.

Connect with Matt @voxmatt on Twitter and LinkedIn.

Thank you so much for joining us in this interview series! Our readers like to get an idea of who you are and where you came from. Can you tell us a bit about your background? Where do you come from? What are the life experiences that most shaped your current self?

In elementary school I made hyper card stacks with Mac IIsi. I loved the possibility of the computer. In school I developed an affinity for history and desire to impact systems at the highest level. Then going to law school and starting in Big Law, where you measure your time by six-minute increments, gave me an appreciation for the preciousness of time.

So, I left law and pursued a career in software engineering in San Francisco. This brought me to several companies, the most impactful of which was RelateIQ. That’s where I met my Clockwise co-founders.

We shared, and continue to share, a common goal: Giving our users more time for focused work, family, and friends. More time that matters to you.

Can you share the most interesting story that happened to you since you started your career?

Shortly after RelateIQ (the startup I was at before I started Clockwise) was acquired by Salesforce, Marc Benioff came down to our office in Palo Alto to attend our quarterly Hack Day. Our offices were in the basement below West Elm on University Avenue. So, first thing, you have to imagine Marc Benioff squeezing into this subterranean startup office and taking roost on a bench at one of the picnic tables in our lunch area — he’s a larger than life character.

As was a personal Hack Day tradition, I presented my demo in character, and this time I had chosen Steve Jobs. Of course, I had no idea when I prepped this that Marc would be there, but every day is a new adventure! So, I was up on stage in a black mock turtleneck presenting God knows what, and here was Marc Benioff questioning me as Steve Jobs (who he knew quite well). It was absolutely surreal and all I remember is him telling me afterwards that I wasn’t quite as good as the real thing, but close. That’s high praise in my book!

What do you expect to be the major disruptions for employers in the next 10–15 years? How should employers pivot to adapt to these disruptions?

It’s hard to imagine any larger disruption in the next 10–15 years than the once-in-a-lifetime disruption we’re seeing right now. At the start of 2020 most employers organized their entire operations around physical office spaces, and now you’re hard-pressed to find any organization that’s going back to the office 5-days a week — much less any employees who want to do so.

What’s more, it’s a highly competitive labor market where employers have to rapidly adapt or face a potential wave of attrition as employees look for greener pastures. So, opinions on remote vs. co-located are almost academic because most employers have a single option: adapt or die.

According to the Future Forum, 93% of employees want flexibility when they work. The future of work is flexible, and employers have to adapt to allow for an employee experience that works in office, remote, at odd hours, at home, in a coffee shop — wherever and whenever your employees can be productive.

The choice as to whether or not a young person should pursue a college degree was once a “no-brainer”. But with the existence of many high profile millionaires (and billionaires) who did not earn degrees, as well as the fact that many graduates are saddled with crushing student loan debt and unable to find jobs it has become a much more complex question. What advice would you give to young adults considering whether or not to go to college?

This is a very situation-dependent question. I wouldn’t trade my college experience for anything in the world. It’s hard to understate the impact my time at college had on my thinking, my growth, my friendships, and my overall perspective on life.

That said, no two experiences are the same. Depending on your career aspirations, the costs may not outweigh the benefits.

As an employer, an applicant’s degree is really only of interest to me for new-grad hires, where it serves as a proxy for experience. Career experience is much, much more relevant when identifying interesting resumes and hiring than is degree. For some fields, like software engineering, I would happily hire a candidate who has no college degree at all, assuming the experience and skillset is there.

Despite the doom and gloom predictions, there are, and likely still will be, jobs available. How do you see job seekers having to change their approaches to finding not only employment, but employment that fits their talents and interests?

Gen Z and millennials comprise nearly half of the full-time workforce in the U.S., and we’re seeing that they think about their career and potential employers very differently from previous generations. According to Gallup’s research, these people are looking for companies that care about their employee’s well-being and have a strong values fit, particularly around diversity, equity and inclusion.

From a job seeker’s perspective, it can be challenging to identify companies that meet these new criteria, so they rely on their network. Now more than ever, there are also ways to find and interact with potential through values-aligned causes and industry groups.

At Clockwise, we end every week with a casual all-company meeting where we show gratitude to coworkers and celebrate things that we accomplished that week. We make it an open meeting, where people can invite friends and former colleagues, and we’ve found it to be surprisingly effective for recruiting because people get to experience the company culture and see our values in action.

The statistics of artificial intelligence and automation eliminating millions of jobs, appears frightening to some. For example, Walmart aims to eliminate cashiers altogether and Dominos is instituting pizza delivery via driverless vehicles. How should people plan their careers such that they can hedge their bets against being replaced by automation or robots?

I agree that we’re entering an era of tremendous technological change. Rather than offering a specific career path to navigate these changes, I believe we need people that know how to learn and adapt. For example, even a leading AI scientist or biochemistry researcher’s skills will be obsolete in 5 years.

In our parents’ generation, it was common for people to have one career for their entire life. I believe that we’re likely to have 3 or 4 different careers, driven by both technological change and longer lifespans. To take advantage of these future opportunities, we need people with a growth mindset, and importantly, we need to give ourselves space to concentrate and practice new skills.

There’s been a dramatic rise in the number of people entering career accelerators and continuing education programs over the past few years, and I’m hopeful that we’ll see more of these opportunities for people as the pace of change accelerates.

Technological advances and pandemic restrictions hastened the move to working from home. Do you see this trend continuing? Why or why not?

I do. There are endless possibilities to bring your team closer together while working remotely. If your company culture was collaborative and fun spirited before the pandemic, then shifting activities that co-workers can do virtually will be less challenging.

There are several ways to build camaraderie while working apart, at Clockwise, we take pride in celebrating our employees and milestones reached. At the end of each week, we gather on Zoom for “demos,” where employees present their accomplishments of the week and if we have reached a particular milestone, we’ll celebrate by wearing silly party supplies like hats or sunglasses.

We also host virtual weekly team lunches for co-workers to chat and catch up. We’ll break up into smaller groups to facilitate conversation and bring everyone together. It’s also important to get employees together off the clock to form bonds and boost morale. Consider organizing a virtual happy hour, game night or some other event that your team will enjoy.

In a remote environment, it’s more important than ever to check-in with your employees and normalize the new landscape as much as possible. For example, we continue to make welcome care packages for our new employees as part of the onboarding process and mail them to their home. Something as simple as this can go a long way to show the company values them.

What societal changes do you foresee as necessary to support the fundamental changes to work?

A broader consensus on childcare being a communal responsibility. The shift to more flexible work has been a benefit to a variety of people, but let’s also acknowledge how incredibly difficult the pandemic has been for parents and, especially, mothers.

Despite a trend towards dual-income households, women are still expected to do the lion’s share of the work inside home and family. There are numerous facets to this problem, but one core element is the expense of, and access to, childcare. If all employees are to benefit from the increased flexibility of work arrangements we, as a society, need to make childcare available and affordable to all households.

What changes do you think will be the most difficult for employers to accept? What changes do you think will be the most difficult for employees to accept?

Impact can’t be measured in facetime. I think it’s very difficult for employers to let go of the old habit of managing by “walking the factory floor.” With employees distributed across geographies, facetime is no longer possible, but I still see a desire among some to move to digital surveillance as a replacement — computer monitoring to record how and when an employee is truly “working.” We need to just let this go; what matters is not input, but output. And any employer who isn’t taking concrete steps towards measuring output is going to be left in the dust.

Similarly, employees should think critically about how they’re agreeing with their employers on what output to measure. Align on targets, goals, and metrics so that you have a clear understanding on how your impact will be measured. It’s no longer sufficient to show up and look busy in the office from 9 to 5.

The COVID-19 pandemic helped highlight the inadequate social safety net that many workers at all pay levels have. Is this something that you think should be addressed? In your opinion how should this be addressed?

Yes, absolutely. As an employer, I do not want to be required to become an expert in healthcare plan administration. I don’t want my competitiveness when hiring to hinge on whether our headcount is large enough to have an employee pool that gets us top-tier healthcare coverage. And, most importantly, I don’t want the health and welfare of my community to hang on everyone having continuous employment. As we’ve seen with this pandemic, health is a community concern, and someone’s access to healthcare shouldn’t be determined by whether, for example, the business owner made a bad decision that requires laying off employees.

Despite all that we have said earlier, what is your greatest source of optimism about the future of work?

My greatest sense of optimism for the future of work is that everyone can be allowed to take back control of their time. Time is something we can never get back, so it’s crucial to maximize it. I’d like to inspire people to question how they really want to spend their days, and empower them to make more informed, more considered choices around how to invest their most precious resource.

Historically, major disruptions to the status quo in employment, particularly disruptions that result in fewer jobs, are temporary with new jobs replacing the jobs lost. Unfortunately, there has often been a gap between the job losses and the growth of new jobs. What do you think we can do to reduce the length of this gap?

It’s an extremely difficult situation. And given that over 5 million people in the United States are out of work due to the pandemic, we’re now starting from an even larger deficit.

Unfortunately, I don’t think shortcuts are going to address the root issues. Fundamentally, I believe that we need to better prepare teachers, children and displaced workers for the skills of tomorrow. To address this gap long term, as a society, we need to invest more in K-12 education, job training programs, and continuing education programs.

Okay, wonderful. Here is the main question of our interview. What are your “Top 5 Trends To Watch In the Future of Work?” (Please share a story or example for each.)

  1. The flexible future of work. Employees who have flexibility when they work report a 140% improvement in stress and work-life balance. The genie is out of the bottle. To attract the best talent, employers are going to need to offer flexible hours and locations going forward.
  2. Burnout boundaries. According to a survey from Deloitte, nearly 70% of professionals feel their employers are not doing enough to prevent or alleviate burnout. Every organization needs to have a plan for how they’re supporting their employees during a time like this. For example, many of the organizations that use Clockwise establish No Meeting Days and dedicated meeting hours to give people time to concentrate and avoid work from bleeding into nights and weekends.
  3. Authenticity in the workplace. The proverbial water cooler conversations at work are changing. More and more, there’s a trend towards employees expecting to bring their whole-self to the workplace, whether it’s their dietary preferences, causes or politics. This trend is one of the reasons that Coinbase’s recent “apolitical” memo was so charged and resulted in 60+ people quitting.
  4. Applied artificial intelligence. Despite the hype from the past few years, we’re seeing very real progress in AI. AI doesn’t look like what you see in the movies. Whether it’s self-driving cars, your Instagram feed, or AI improving crop yields, we’re starting to see valuable specialized applications of AI in everyday life, and this trend is not going away.
  5. Decentralized control. Across both technology and business culture, I’m seeing a clear trend towards mission-oriented and autonomous decision making. Decentralization is a fundamental property to most popular blockchain projects, but we’re also seeing increasing decentralized decision making at very large organizations like Amazon and Google, as they continue to scale and push into new markets.

Can you please give us your favorite “Life Lesson Quote”? Can you share how this quote has shaped your perspective?

“This is water.” David Foster Wallace’s 2005 commencement speech is a piece I return to often. The speech, which you really should read in its entirety, is a critical, always relevant, reminder of the central importance of empathy and the very real choice we have in choosing how to engage in the world around us.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

Professor Cal Newport. Newport’s writings on deep work, organizational productivity, and the future of work are must-reads for anyone running a modern business. It’s been a while since we’ve caught up; drop me a line!

Our readers often like to follow our interview subjects’ careers. How can they further follow your work online?

Twitter: @voxmatt

Thank you for these fantastic insights. We greatly appreciate the time you spent on this. We wish you continued success and good health.