Ask an Investor: How do I manage remote workers?

employees working

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Amazon made a splash went it put out a call for municipal HQ2 bids, but opening a satellite office is nothing new for modern tech companies. Talent is the most important, and scarcest, resource for startups — the difference between success and stagnation is the caliber of team you’re able to attract. In the search for this talent, startups often expand into another geography to attract experienced salespeople, designers, marketers, and developers. But attracting those employees is the easy part — retaining and managing remote office workers is where it gets tough.

I know this first-hand, as I joined iNovia as a remote worker. We have a distributed team model, with employees in six cities, three time zones, and two countries. Maintaining a cohesive work culture as you expand beyond one office will depend on your unique company values, the number and size of offices, and the seniority of those employees. However, the specifics will all be governed by two core principles – transparency and inclusion.


As whiteboards become digital dashboards, it’s easy to assume that everyone on the team is on the same page about company health and strategy. In my experience, you should consciously set up all work processes to revolve around shared tools. Google Drive is an easy and affordable toolset; we build budgets and forecasts in Sheets, work on job postings and investment theses in Docs; and draft a marketing schedule in Calendar. Trello or equivalent tools are great for task management, shared Wunderlist lists keep everyone aligned on to-dos, and shared Evernote or Dropbox folders keep working notes organized.

An important principle here is openness: since we can’t physically call a coworker over to our laptop screen or show them our schedule at a glance, we default to open settings that let teammates stay aware without waiting for permission.

An important principle here is openness: since we can’t physically call a coworker over to our laptop screen or show them our schedule at a glance, we default to open settings that let teammates stay aware without waiting for permission. We also keep calendars open, so people can easily book meetings without extensive back-and-forths (and so it’s obvious when a coworker in a different time zone is at a school recital or family dinner).

There are great purpose-built tools to track and manage the key inputs that drive your business model. Startups and new investments are our life-blood, so we invest extra in Affinity, a VC-specific CRM that puts collaboration front and centre.

For a sales-oriented company, a proposal management tool like PandaDoc might be a better investment. If time zones make weekly stand-ups challenging to schedule, consider tools for goal setting. An OKR platform like Perdoo keeps your whole team aligned on quarterly company objectives, how objectives for each team member (or department) feed into those top-line objectives, and how the team’s key results are tracking against them.


Humans are social creatures, and we value inclusion not just for the chance to be part of a group, but also for how we feel it reflects people’s opinions of us. Given the emotional dynamics at play, aim for over-communication and nailing the little things.

Set everyone up with the tech basics

Culture is defined by the daily actions we take, rather than a written statement.

Remote offices don’t always have an office manager, but make sure that your employees feel equipped. Second screens, keyboards, and mouses can get forgotten, but have a huge impact on turning a small WeWork desk into an office space.

Chat software, remote meeting software, tele-presence devices, separate webcams, and access to a private conference room make communication seamless and help bridge the miles between offices.

Aim for equality of events

Free breakfasts or lunches, afternoons off to volunteer, fireside chats with senior management and/or special guests – these are all perks that companies will occasionally schedule at HQ to keep employees engaged and celebrate company milestones. Anything that’s scheduled for HQ should be happening at HQ2 – deliver breakfast to all your locations, and stream your guest presentations to remote workers.

Audio/video > Slack > email

Facial expressions, body language, and tone of voice play a huge role in communication. Aim to pick up the phone or video call — it’s typically faster and less prone to miscommunication. When Slacking or emailing coworkers, accept that there’s a higher chance they’ll agonize over hidden subtext or misinterpret tone.

Some of our portfolio companies have taken this a step further, with a permanent live video feed running from all the offices so people can see their coworkers and what they’re doing. Even on mute, it’s nice to see that your coworkers are real people who are all part of the same team.

Celebrate the positive

Feedback tends to shrink for remote workers. Picking up the phone or sending a feedback email can feel overly formal, meaning it slowly becomes a tool only used for constructive criticism that needs to get delivered.

Positive recognition often happens verbally and informally. If an employee can’t physically ring the sales bell in front of the whole team, or get called out during a Friday afternoon debrief, circulate an email recognizing them to their peers to make sure feedback isn’t disproportionately critical.

Encourage random conversations

When you’re working from a secondary office, you tend to miss out on “random collisions” that otherwise happen when all employees are housed together. Without a water cooler to cluster around, or a hallway to bump into colleagues in, informal conversations and spontaneous collaboration fall by the wayside.

We have a #random channel in Slack where people are encouraged to post the topics that are dominating their mindshare, which would otherwise come out in those informal conversations.


Schedule together time

Once a quarter, my team hosts full team retreats, where we all spend a few days in the same city to set our strategy, prioritize our goals for the quarter, and spend quality time over meals and adrenaline-pumping activities.

Individual team members aim to visit coworkers in other cities every month, nurturing those individual relationships and checking in on relevant projects in person. The cadence that’s right for your firm will depend on the size and seniority of your remote employees. The more senior an employee, the more time they typically spend travelling. Don’t restrict travel to your one remote VP — the executive team should occasionally travel to other offices, focusing on engaging with the team there, understanding the pulse of the office, and hosting fireside chats or all-hands meetings to replicate the exposure to senior management that employees at HQ naturally get.

Get conscious of time zones

Remote workers tend to work longer days. They schedule a full work day with clients, co-workers and partners in their same time zone, but frequently get scheduled into off-hours meetings with team members in other geographies. Pay extra attention to bandwidth and burnout for cross-geography teams, especially when most of the team members work in the same time zone.

Encourage employees to block off personal time to serve as a deterrent for meetings scheduled outside of working hours.

Respect time zones

Block off holidays in your master calendar and respect that employees in Ontario will be taking Family Day a week later than employees in BC. Encourage a culture where people take the holidays as they occur, rather than banking an extra PTO day. Holidays are about more than the time away from work – they’re typically community or family events, and an extra day of vacation is a poor reward for working through a Memorial Day neighbourhood event.

Ultimately, get creative! Culture is defined by the daily actions we take, rather than a written statement. Employees at all levels of the organization can impact the relationship between different offices, and whatever empowers your team to feel satisfied with a remote work model is the right strategy for you.

Christian’s take:

Christian Lassonde

Almost every company in tech today has at least one member who works at least part of the time virtually. Impression Ventures is no exception. Our head office is in Toronto, but we have a satellite office in Montreal. It’s a good reminder that even if you don’t think of your company as using a distributed team model, you likely have members who aren’t at the head office.

If that’s the case, Sarah’s best practices above all still very much apply. It’s a good corporate New Years resolution to take stock of where all your employees are based out of. Even if you only have one or two employees who work part-time virtually, consider carefully if they are being treated as full equal coworkers to your head office staff. Sarah’s take provides a wonderful starting point to increasing happiness and performance out of all of your team.

Photo via Unsplash

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Sarah Marion

Sarah Marion is an Associate at iNovia, a full-stack venture capital firm that partners with audacious founders to build enduring technology companies. iNovia manages $500M across three funds, and holds offices in Montreal, Toronto, San Francisco, and London. For more information, visit

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