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Peter Jackson of Bluescape: Five Things You Need To Know To Successfully Manage a Remote Team

In 1994, I was tasked with managing six different divisions of operations and consolidating company spend. To do this effectively, I had those teams work from home. We didn’t have Zoom (it was still the age of the fax machine), but luckily, we had great people in the field who had strong relationships with clients. A learning I took away from that part of my career and am applying to my company today is how important it is to stay engaged, even though it’s more difficult to communicate.

As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing Peter Jackson, CEO of virtual workspace software company Bluescape.

Peter Jackson is a serial entrepreneur and advisor with a broad and deep knowledge of technology, business, and financial markets. Prior to Bluescape, he co-founded Ziploop Inc. (acquired by SNIPP in October 2017), served on the Boards of Eventbrite, DocuSign, and Kanjoya; took Intraware to IPO, and was President/COO of Dataflex (NASDAQ. DFLX) following its acquisition of Granite Systems, among other achievements.

Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit better. What is your “backstory”?

Briefly touching on my childhood, I was born and raised in Berkeley, California, where my mother taught deaf and blind students from our home. There, I grew up quite imaginative, and was always dreaming up inventions and businesses, and taking up small jobs wherever I could find them.

My first real job out of college was as an associate in sales at a company where they’d hire 10 people and then immediately fire seven. In that working environment, I taught myself to work smart versus more. While others were making 100 calls a day to make their sales, I would focus on 10 accounts by connecting with my customers in unconventional ways. Instead of working overtime to hit personal call quotas, I’d leave the office to go where I knew my clients spent their free time to make actual relationships. I went from being #400 to #1 salesperson in less than 2 years.

From there I co-founded two companies, Ziploop and Intraware, even taking Intraware to IPO. Additionally, I have served on the Boards of Eventbrite, DocuSign, and Kanjoya; and worked as President/COO of Dataflex.

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

At my first sales job, everyone was working like crazy. But like I said before, I prioritized just 10 accounts and honed in on the actions that made me the most productive. For example, if I knew that some of my clients were going to be at a soccer game, that’d be my office for the day. By looking at what I had to do to sell over what was perceived as the ‘office norm,’ I made myself the #1 salesperson.

This forever shaped my belief that the future of work is a future where we can accomplish our responsibilities on our own terms. If someone can complete what they need to do for that week more swiftly, they should not be bound by geographical or 9-to-5 time restraints.

Years following my first position in sales, I met a man who was told by his company that he needed to work 40 hours a week. He asked them if he could choose which 40 hours he worked — and they said yes. He would start his work on Sunday and work up to Wednesday so that he could spend the rest of the week with his family. He was given the freedom to create his own schedule, but even more, he proved that work can be task- or outcome-oriented versus time.

Much like the geographical restrictions that we’ve unbound ourselves from during the COVID-19 pandemic, I believe that we should free ourselves from the traditional 40-hour workweek. If workers can complete their day’s tasks in 5 hours, why should they sit at their desk and twiddle their thumbs? At my company, we’ve cultivated a culture prioritizing outcomes, independent of assumptions about time and place.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

This story started as a mistake and resulted in altering my status at my first job. It was a Friday night and I was grabbing a bite after work when I saw another gentleman who immediately started engaging with me in conversation. Halfway through the chat, he said, “Man, I’m so sorry but I have to tell you why I’m so happy.” I had time to spare, so I told him I was all ears. That’s when he told me he just won a major contract for scanning equipment for every grocery store in Canada, to be followed by the U.S.

I offered to buy him a drink to celebrate, but he instead insisted on buying me a round. He asked what I did for a living and I told him that I was in tech, selling equipment that big providers couldn’t manage. He lit up and said, “I just made your life” and instructed me to meet him Monday morning in front of that same restaurant for a meeting.

On Monday morning, he picked me up in front of the restaurant to meet with one of his partners. Upon walking into the office, his partner hands me a huge stack of paper, easily worth $35 million in orders. I was making about $30K as a salesman back in 1983 and my company ended up making $20 million from that deal, bringing me to the #1 salesman.

The learning from that night was simple: You can meet anyone, anywhere.

What advice would you give to other CEOs or founders to help their employees to thrive and avoid burnout?

As a nation, we’ve all been working non-stop from our homes due to coronavirus. Teams are struggling to disconnect, especially as companies become more decentralized and work across various time zones. While we’re bound to our homes, we still need time off to prevent burnout and boost productivity.

Comparing 2019 to 2020, employee PTO requests have reduced by nearly half. However, employers are juggling more than ever — ranging from personal burdens to new ways of working to the emotional and physical toll of today’s many pandemics. Employees need to take a break and it’s up to business leaders to create the space for them to do that. Even before the pandemic, 2 out of 5 employees felt that time off to address their personal lives would negatively influence their futures. This is why the responsibility lies in business leaders to be flexible and support their employees for long-term success. The first step is rethinking company PTO policies. Whether that means unlimited PTO, creating new company holidays, or even planning company-wide mental health days, these new policies will provide employees with the space — and trust — needed to take much-need time off.

Ok, let’s jump to the core of our interview. Some companies have many years of experience with managing a remote team. Others have just started this, due to the COVID-19 pandemic. Can you tell us how many years of experience you have managing remote teams?

In 1994, I was tasked with managing six different divisions of operations and consolidating company spend. To do this effectively, I had those teams work from home. We didn’t have Zoom (it was still the age of the fax machine), but luckily, we had great people in the field who had strong relationships with clients. A learning I took away from that part of my career and am applying to my company today is how important it is to stay engaged, even though it’s more difficult to communicate.

Managing a team remotely can be very different than managing a team that is in front of you. Can you articulate for our readers what the five main challenges are regarding managing a remote team? Can you give a story or example for each? Based on your experience, what can one do to address or redress each of those challenges?

Managing remote teams can be challenging, especially if you don’t have the proper tools to communicate, collaborate, and track team projects. Layer in the fact that, for many, this is the first time they are working remotely — and had to adapt practically overnight. With new management styles, technology, and even home offices, here are a few of the biggest challenges I’m seeing:

  • Managing progress without exhausting teams with “catch-up” meetings. We’ve all experienced ‘Zoom-fatigue’ and this is seen even in our personal lives with the disappearance of Zoom happy hours! Attending these virtual meetings take up more energy and focus than in-person meetings, so traditional phone calls or even regular email updates can make up for this. Reserve video conferencing for in-depth discussions/brainstorms or when you need quick updates in real-time.
  • Accessing, collaborating, and finalizing content, remotely. Even in the office, teammates may ask each other, “Do you remember where this document was saved?” However, in the office, responses are much more prompt. By centralizing all of your content, remote teams don’t waste their time and energy to search and toggle between documents and applications.
  • Engaging teammates during virtual meetings. Allow team leaders to focus on delivering key information while designating a moderator to run the meeting, focus on asking questions, and engage each member of the team. This balances the participation rate and ensures everyone has an equal share of voice.
  • Developing feelings of stress and tiredness from long hours. Many reports show that we’re productive only 3 hours a day. Yet, we are still transitioning from the era of punching the clock for compensation. This approach has not credited employee efficiency and has slowed production. Rather than tracking time, record milestones and deadlines and reward for the effective completion of assignments.
  • Creating secure best practices to prevent cyberattacks. Remote work has created several vulnerabilities for company data and employee personal data and privacy. Creating best practices with regular reminders to employees will empower teams to stay vigilant while navigating online.

In my experience, one of the trickiest parts of managing a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. Can you give a few suggestions about how to best give constructive criticism to a remote employee?

When giving feedback to a remote employee, you want to be clear enough so they understand there is an issue at hand. However, you also want to ask them questions about how they feel about the situation and discuss processes and suggested actions moving forward. Asking your employees questions about how they feel about the feedback and how they got to their situation will help make up for the body language/physical gap created by today’s remote work environment. It’s also important to discuss work processes, as employees are confronted with a new working environment. Maybe they are used to ad hoc brainstorms with their neighboring office mates, but no longer have the creative outlet to have these discussions. Business leaders must always remember to foster growth in their feedback and criticism.

Can you specifically address how to give constructive feedback over email? How do you prevent the email from sounding too critical or harsh?

Honestly, I don’t recommend giving constructive feedback solely over email, unless they’re factual or quantitative. Even when it comes to one-off employee performance feedback, I think managers should address these during 1:1 meetings to get an employee’s real-time reactions and thoughts. Emails can provide space for different interpretations and for feedback to be constructive, it must be concise. However, after 1:1 discussions, managers can summarize the discussion and feedback in an email to their employees as a record of the conversation and a way to align on concrete next steps.

Can you share any suggestions for teams who are used to working together on location but are forced to work remotely due to the pandemic? Are there potential obstacles one should avoid with a team that is just getting used to working remotely?

While we are learning to live with today’s global pandemic, we’re also learning how to work in new ways. COVID-19 is pushing businesses to integrate remote work technologies to keep their companies running, employees productive, and customers served — all while implementing company-wide remote work policies for the first time. Some of the challenges companies should be aware of, and ways technology can help, include:

  • Maintaining visibility on important business initiatives. In a remote setting, it takes more effort to get team updates on projects, especially since we aren’t able to drop into a coworker’s office. This is where the right technology can help executives keep a pulse on projects and team members by tracking deliverables, timelines, and budgets from a singular workspace platform.
  • Lacking access to important data. Finding information saved in the cloud by other colleagues can be frustrating even when working in the same office. Unfortunately, progress and timely decision making are compromised when documents aren’t more easily retrievable. Again, be sure to put into place a technological solution that makes it easy for authorized employees to find what they want and when they need it.
  • Transitioning the company culture during a global crisis: While COVID-19 is transforming the business landscape, what companies are doing in response should not be viewed as temporary. Remote work is shifting company culture and going back to “business as usual” will be disruptive. As the virus abates and people return to the office, companies need to have a plan in place around the long-term future of remote work.

What do you suggest can be done to create a healthy and empowering work culture with a team that is remote and not physically together?

I make a conscious effort to check in on every single one of my employees at least once a week, usually through Slack. With a quick message, I can see how they’re doing and how they are working. At Bluescape, we also have weekly town hall meetings where I try to engage everyone with a fun trivia question and a cool reward.

I think that making each employee feel appreciated and heard is the best way to boost morale and productivity. I really believe success is about productivity, not time. Productivity leads to the business making money, and to do that, your workforce needs to feel like they have the right tools, whether its education, technology, environment — or especially mental health. Again, business leaders need to put employee well-being at the forefront of their decisions, especially during this critical inflection point.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

From my perspective, the movement I try to stress is that your opinion — whatever that is — is very important. It’s not my job to judge your opinion or feelings, but to listen and try to understand what you are expressing and experiencing. I think to be compassionate and really listening and processing what people are saying and feeling can be very powerful, especially now.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

You must have honesty and integrity. People can read your eyes and will gravitate towards you if they believe in what you stand for. I think, right now amid COVID-19 and remote working, this becomes difficult. It’s hard to read people on Zoom and get the right body language. That’s why it’s more important now than ever to have honesty and integrity.

Thank you for these great insights!




In-depth Interviews with Authorities in Business, Pop Culture, Wellness, Social Impact, and Tech. We use interviews to draw out stories that are both empowering and actionable.

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Fotis Georgiadis

Fotis Georgiadis

Passionate about bringing emerging technologies to the market

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