Dr. Gleb Tsipursky – The Office Whisperer
Nirit Cohen – WorkFutures
Angela Howard – Culture Expert
Drew Jones – Design & Innovation
Jonathan Price – CRE & Flex Expert
- Distributed work offers access to diverse talent, cost optimization, and lifestyle benefits.
- Challenges include fragmented communication, isolation, and measuring productivity.
- Success in remote work demands intentional design, proactive strategies, and strong leadership.
The future of distributed work is not a question of where people sit, but rather a matter of how deliberately organizations design their work environments. In a candid conversation with me, William West, Vice President of People at Wrapbook, laid out a compelling case for why intentionality must guide the evolution of remote and hybrid work.
West, who has spent over 15 years shaping HR strategy across various organizations, brings both a strategic and deeply human lens to the challenges and opportunities of flexible work.
The Case for Going Distributed
Wrapbook, a financial services platform for the entertainment industry, made a strategic choice to build as a distributed organization, with employees spread across the U.S. and Canada. For West, the benefits are clear: access to broader talent, deeper DEI, and smart cost optimization.
Hiring across geographies has allowed Wrapbook to go beyond tech industry hotspots, tapping into exceptional talent often overlooked by coastal firms.
“We’re not just trying to replicate the Silicon Valley model,” said West. “We’re building a team that reflects our mission and values.”
That access to diverse perspectives and lived experiences is critical for serving Wrapbook’s varied client base in entertainment, which is an industry that thrives on creativity and inclusivity.
From a cost standpoint, the math is simple but powerful. Remote work enables companies to hire in lower-cost cities while maintaining high standards. That’s not just about saving dollars; it’s about deploying capital more strategically.
West emphasized that while they’ve kept the team within North America for cultural cohesion and communication alignment, they’ve still found ways to reduce operational costs without sacrificing quality.
On a personal level, West noted the lifestyle transformation that flexible work enables.
“We got a puppy this year — that wouldn’t have been possible if I worked in a traditional office setup,” he shared. Beyond lifestyle perks, flexible work has sharpened his focus and time management. “When I can control my environment, I can be far more intentional with my time.”
The Friction Behind the Freedom
Yet West is quick to point out that distributed work isn’t without its challenges. He identified three key friction points that require ongoing attention: incomplete context, social isolation, and measuring productivity.
The first challenge of fragmented communication arises from what West calls “incomplete stories.” In a remote setting, employees often receive snippets of conversations via Slack, Zoom, or shared documents.
Without the serendipitous interactions of an office, it’s easy to misinterpret or fill in the gaps with assumptions. When things are going well, those stories remain optimistic. But when uncertainty creeps in, mistrust and miscommunication can grow.
That lack of context also feeds into the second challenge: loneliness.
“It can be really isolating,” West admitted. “My wife and kids are out during the day, and there are times I don’t see anyone in person for hours.”
This emotional gap affects more than morale. It can erode team cohesion and, ultimately, retention. Employees who feel disconnected are less likely to weather tough periods or invest in long-term commitment.
The third challenge is one every distributed leader wrestles with: measuring output. In a remote environment, trust is essential, but it must be balanced with systems that track real contribution.
“You need more intentionality around evaluating productivity,” said West. “It’s not just about trusting that work is getting done. It’s about defining and measuring what success looks like.”
Designing Connection on Purpose
So how do you counter those challenges? According to West, it starts with talking about them openly and designing your work culture with intentionality, not convenience.
Wrapbook has leaned into proactive strategies, starting with company-wide conversations about the pitfalls of remote work.
“We hosted an hour-long session just on incomplete stories — why they happen and how to prevent them,” West explained.
By addressing the issue before it became a problem, the company built shared awareness and language around the dynamics of distributed communication.
But words only go so far. In-person touchpoints are a critical supplement. Wrapbook organizes regular offsites, including company-wide retreats in places like Cancún.
“Those few days of face-to-face interaction pay dividends for months,” West said.
At the team level, smaller gatherings help managers and employees build the trust needed to sustain collaboration across distance.
West also highlighted the importance of cadence, especially when it comes to communication. Where a quarterly all-hands might have sufficed in an office, Wrapbook now runs monthly sessions to maintain alignment and reinforce the company’s narrative.
The focus isn’t just on transmitting information but on creating shared meaning.
The People Leader’s New Mandate
Central to all of this is the role of the manager.
“Companies are made or broken by how well they equip their managers,” West emphasized.
Wrapbook invests heavily in manager training, with a specific lens on the demands of remote leadership. That means teaching leaders to be proactive communicators, empathy-driven listeners, and clear translators of company strategy.
One standout practice: Wrapbook provides managers with not only performance data and strategic updates but also explicit instructions on how to cascade that information to their teams.
“We give them the ‘what’ and the ‘how,’” said West. “That way they’re not spending energy decoding it themselves.”
Video communication has also emerged as a critical tool.
“Seeing someone speak — even on a screen — adds tone, body language, and emotional nuance you just can’t get from text,” West noted.
This change to video messaging, championed by both West and host Dr. Gleb Tsipursky, can reduce meeting fatigue while maintaining human connection.
These systems, West argues, aren’t temporary adaptations. They’re the foundation of a well-designed distributed culture.
The Future Will Favor the Intentional
As debates swirl around return-to-office mandates and hybrid compromises, West remains clear-eyed about the future of work.
“The organizations that succeed in remote work will be the ones that build it with intentionality,” he said.
Simply repackaging old habits into digital formats won’t cut it. The future belongs to those willing to rethink everything, from meeting structures to performance metrics, with clarity and purpose.
West believes that distributed work, especially for fast-growing and cost-conscious companies, is advantageous. But success requires more than policy changes, demanding a systemic redesign of how teams communicate, connect, and collaborate.
In short, intentional design isn’t just a fix for the flaws of remote work, but is instead the blueprint for a new kind of workplace — one built not on location, but on deliberate, human-centered systems.
As Wrapbook’s experience shows, when you build with intention, you don’t just keep up with change — you lead it.
