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Remote Career Development: Sara Cooper Of Jobber On How To Advance and Enhance Your Career When You Are Working Remotely

An Interview With David Liu

Communication. As much as we all have Zoom fatigue, it’s still important for teams to see each other regularly. A quick 15-minute meeting a couple of times a week that doesn’t involve shop talk is all it takes!

Career development is the ongoing process of choosing, improving, developing, and advancing your career. This involves learning, making decisions, collaboration with others and knowing yourself well enough to be able to continually assess your strengths and weaknesses. This can be challenging enough when you work in an office, but what if you work remotely? How does remote work affect your career development? How do you nurture and advance your career when you are working from home and away from other colleagues? How can you help your employees do this? To address these questions, we started an interview series called “How To Advance and Enhance Your Career When You Are Working Remotely”. As a part of this interview series, I had the pleasure of interviewing Sara Cooper.

Sara Cooper is the Chief People Officer at Jobber. She spent over 15 years in Toronto’s tech industry in companies from early-stage startups to enterprise organizations. Her most recent role prior to joining Jobber was with OMERS Ventures, one of Canada’s largest investors, where she was responsible for advising a portfolio of close to 40 high-growth companies on their HR & Talent strategies. During her time at OMERS Ventures, Sara released the Start-up Talent Playbook, which was embraced by Canada’s startup ecosystem, and also built a mentorship network connecting startup employees with executives at other companies for professional development. Sara also helped grow and guide teams at Softchoice, Lavalife, and Microsoft, and held leadership roles at D+H and FreshBooks, which more than doubled in size during her tenure.

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”?

I’ve spent more than 15 years in Canada’s tech industry across companies ranging from early-stage start-ups to enterprise organizations, including Microsoft, FreshBooks, and now Jobber. Throughout my career, I have experienced everything from high-growth to no-growth, lay-offs, multiple pivots, and several M&As. I also spent several years with OMERS Ventures, a venture capital fund investing in disruptive tech companies, where I advised 40+ high-growth portfolio companies as they built strategies to attract, retain, and develop their talent as they grew businesses. These experiences have allowed me to have a unique view on businesses and how they develop (or not) and how vital it is that people strategies stay business aligned to ensure the best possible outcomes.

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

My role with OMERS Ventures was a great experience that allowed me to work with such a wide range of different companies at all different stages, and with some absolutely brilliant founders with incredible visions. Working alongside such a wide variety of portfolio companies that represented some of North America’s most promising and successful tech companies meant that one day I could be advising a founder on how to hire their very first developer and advising another on global hiring plans the next. There was never a dull moment!

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?

Early in my career, I had just begun a new role and wanted to make an immediate good impression. I decided to completely overhaul the interview and hiring processes for our tech group to make it (in my mind, anyway) more streamlined and efficient. I did this without actually talking to anyone about it or verifying if my initial impression of the processes was correct. When I was finished, I booked a meeting with the CTO to present it. The first question he asked was, “who did you partner on this with?” and we then had an illuminating discussion on why it was important not to create things in a silo.

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

I don’t have a specific quote that I can attribute to someone, but I do live by the phrase “make other people successful.” This has been a guidepost for me personally and professionally. In some ways, it’s another alternative to a more familiar quote that we’re all familiar with: “a rising tide floats all boats.” The point is that, if everyone is focused on making those around us successful, we ultimately all win.

What advice would you give to other business leaders to help their employees thrive and avoid burnout?

Burnout has never been a more important topic for leaders at all levels to address — and increasingly is a key factor in retaining top talent. There’s several specific steps that people-leaders can take to overcome burnout.

  • Set clear expectations on both sides. It’s important for employees to be able to switch off and it’s equally important for employers to show that switching off is expected and encouraged.
  • Encourage open discussions about mental health challenges. Dedicate mental health sources to support the holistic development of employees, helping individuals confidentially overcome some of the challenges impacting their personal lives first.
  • Ensure vacation time is booked, taken and respected. It’s there for a reason, and doesn’t just allow employees to take a mental break, but also return refreshed and able to be most productive.

Ok, let’s jump to the core of our interview. Working remotely can be very different than working with a team that is in front of you. This provides great opportunities but it can also create unique challenges. To begin, can you articulate for our readers a few of the main benefits and opportunities of working remotely?

We have found amazing talent that we wouldn’t have otherwise if we were to require everyone to return to a physical location. Empowering our workforce with the ability to decide where they would like to work has increased the diversity of our teams, and led to better creativity and opportunities for different discussions.

However, we also realized early on that there’s no single hybrid solution that would work for everyone — some employees wanted to return entirely, many wanted to remain fully remote, and others preferred some combination of both. The key to creating a successful environment requires the input of a company’s most important stakeholders: its workforce.

Rather than making a top-down decision about what hybrid approaches should look like, companies should be willing to propose initial ideas and adapt them to what works best for each company and their employees. Embracing this style of communication is critical to the hybrid model as it evolves over time to meet the needs of employees.

Can you articulate for our readers what the five main challenges are regarding working remotely?

As more companies begin to shift to hybrid models or remote-first approaches, many are encountering similar challenges:

  • Connection. People crave it and it’s far easier for folks to leave companies when they don’t feel a connection to their colleagues or leadership.
  • Communication. We live in a world where we are communicating mainly by text. You lose tone and body language cues that can help with messaging.
  • Creativity. Some work is better done together and remote tools aren’t always as effective for group creative work like brainstorming.
  • Always On. When you work mainly (or completely) from home you have to be very diligent with your down time. It’s easy for work to creep into every aspect of your life. Which leads to the next concern…
  • Burnout & Mental Health Concerns. If you don’t create solid boundaries for yourself or if your employer doesn’t respect your boundaries you run the risk of the “always on” mentality burning you out.

Based on your experience, what can one do to address or redress each of those challenges? Can you give a story or example for each?

Below are the solutions that have allowed us to remain successful, regardless of the approach moving forward:

  • Connection. Provide opportunities for folks to connect in a way that doesn’t feel forced (i.e. those dreaded Zoom cooking classes!). We provide a lot of optional activities that people can join virtually but also give opportunities for folks to get together one-on-one, either in person or virtually through our “Coffee Tag” program.
  • Communication. As much as we all have Zoom fatigue, it’s still important for teams to see each other regularly. A quick 15-minute meeting a couple of times a week that doesn’t involve shop talk is all it takes!
  • Creativity. When our offices reopen, we’ll have more breakout areas for teams to get together for this type of work but, until then, we use the virtual tools that are available.
  • Always On. Ensure that folks know that they are not expected to always be available. At Jobber, everyone has four “overlap hours” that we’ve picked so no one has to start work before 9:00 a.m. or finish after 5:00 p.m. in their time zone. Outside of those hours, employees can pick their own schedules and have those hours listed in their calendars.
  • Burnout & Mental Health Concerns. Being open about mental health challenges and making it a safe thing to discuss is important. We support our People Leaders in having those conversations and ensure that employees have a healthy work/life balance.

Let’s talk about Career Development. Can you share a few ideas about how you can nurture and advance your career when you are working from home and away from other colleagues?

I would encourage people to be open with their people-leader about their development goals and specifically work on a plan with them to help you get there. While I do believe that each person is always responsible for their own development, their people-leader should be able to provide the opportunities for them to reach their goals. That might be through stretch assignments, cross-functional work or skill-specific training opportunities.

It’s also important to ensure that you’re having regular check-ins on the plan and measuring that progress. If things appear to be slipping, have a discussion as to why that might be and what is needed to help support you in reaching your goals.

Can you share a few ideas about how employers or managers can help their team with career development?

Employers need to prioritize development. It’s a great talent attraction and, just as equally important, retention strategy.

At Jobber, we recognize the importance of investing in employees’ careers, and are committed to growing the skillsets of every single employee while they’re with us. To best support learning and growth for employees at all levels, we have combined our Learning & Development and Coaching disciplines into a single function.

The team includes a Manager of Learning & Development, a Learning Specialist, and two full-time Career Coaches. They work together to provide employees with a dynamic framework that helps guide employees throughout their careers at Jobber levels and defines career paths for all departments, coaching, and growth-focused development plans.

Doing so has reframed the traditional concept of a ‘corporate ladder’ into a ‘career jungle gym’ that highlights the diverse growth opportunities available for all employees — whether that’s taking on more responsibility, shifting into an entirely different role, or simply focusing on doing the best job possible in a current position.

While not every employer has the ability or resources to set up full Learning and Development teams, putting a budget towards development, having clear career paths and ongoing development discussions with employees can make a huge impact.

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. :-)

Personally, I do truly believe that having employers invest in their employees would have a profound impact. People spend so much time at work — they invest their time, their talent and their energy in companies and so often they get little to no investment back in themselves.

Invest in your people. Develop them. Support them. Do this because it’s a smart business decision from a recruiting and retention standpoint, but also because it’s simply the right thing to do.

How can our readers further follow your work online?

Feel free to connect with me on LinkedIn:

Thank you for these great insights! We wish you continued success.



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