By Dr. Gleb Tsipursky 

At the epicenter of a rapidly transforming work landscape, Upwork has been leading an ambitious integration of generative AI into the heart of its marketplace. Dave Bottoms, GM Marketplace and SVP of Product at Upwork, described in an interview with me the organization’s journey as a decisive response to the disruptive emergence of ChatGPT at the end of 2022. Rather than approaching Gen AI as merely a tactical addition, Upwork saw it as a fundamental driver reshaping both talent productivity and the structure of work itself.

The company quickly established Upwork Labs, a dedicated experimental group tasked with identifying and implementing AI across its platform. A key early initiative was an AI-driven job post generator, a tool that automatically crafted optimized job postings using machine learning models. This innovation dramatically accelerated the hiring process by simplifying job post creation and enhancing discoverability, reflecting Upwork’s broader philosophy: use AI to eliminate friction without undermining the human element.

Internally, the Upwork engineering teams piloted GitHub Copilot to boost productivity, initially focusing on zero-to-one projects with minimal interdependencies. Over eighteen months, this cautious experimentation blossomed into adoption across nearly all teams. Developers embraced AI tools as productivity enhancers rather than job threats, transforming check-in rates, deployment velocity, and overall cycle times. Daily deployments, once an aspiration, became the new standard, improving scalability, reliability, and bug rates across the board.

Designers Step Into Production with Gen AI

Perhaps the most surprising development, Bottoms noted, is that designers—not just engineers—have begun producing production-level code through Gen AI tools. Upwork’s design teams, rooted in platforms like Figma, are now leveraging emerging features such as Dev Mode to export high-fidelity prototypes directly into code ready for deployment. This leap represents a fundamental shift: designers are no longer merely suggesting user experiences; they are building them.

The rise of this capability signals a profound evolution in the role of design. Traditionally, wireframes and mockups were translated into specifications that engineers would interpret. Now, designers can rapidly test, validate, and implement ideas without the intermediary step, dramatically accelerating product iteration cycles. The impact on productivity and creative agility is striking, with designers engaging in a level of technical execution previously reserved for engineers.

Alongside designers, product managers at Upwork are also experimenting with Gen AI to prototype and validate concepts faster than ever. The tools available today allow product thinkers to move from an idea to a functional demonstration in record time, setting a new tempo for innovation across the organization.

Balancing Productivity Gains with Workforce Anxiety

Despite the clear productivity advantages, Upwork acknowledges the anxiety that Gen AI adoption stirs among both internal teams and freelance talent on its platform. Developers initially worried about displacement are now largely reassured given Upwork’s focus on AI as a companion, not a competitor. True value remains rooted in understanding customer pain points, system architecture, and the nuanced application of technology—skills that no AI has yet mastered independently.

Among Upwork freelancers, similar shifts are underway. Categories like writing and translation have seen changes in human demand, as AI tools have automated many basic tasks. However, new opportunities have risen for those willing to adapt. Instead of straightforward translation, the platform now sees demand for local language experts who can fine-tune AI outputs to ensure cultural and linguistic authenticity. In writing, the emphasis is shifting toward editorial oversight, quality assurance, and SEO refinement rather than original content creation alone.

Bottoms emphasized that freelancers who master AI-enhanced workflows are not just surviving; they are thriving. They move up the value chain by increasing their project volume and ensuring higher-quality outcomes. In a sense, AI has expanded the definition of expertise itself, rewarding those who can both collaborate with machines and provide human judgment where it still matters most.

Charting a Future of Humans Plus AI

Looking ahead, Upwork’s vision is clear: the next three to five years will be defined by a powerful synergy between humans and AI. Upwork’s mindful AI, Uma,  already powers smarter client-freelancer matching. But the ambitions go further. Bottoms envisions a future where not just humans, but agentic AI entities operate within the marketplace, acting on behalf of clients and freelancers alike.

Clients might one day deploy AI agents to search for talent, review freelancer proposals, and even collaborate on project management. Freelancers could have AI assistants finding jobs, preparing applications, and managing client communications. Upwork’s two-sided marketplace is poised to evolve into a richer, more complex ecosystem that remains deeply human but vastly more efficient.

Through it all, Upwork’s commitment to responsible AI use remains paramount. Rather than replacing humans, the company is empowering individuals to become more capable, more productive, and more valuable. As designers push into coding, as engineers deploy daily, and as product teams innovate faster than ever, one truth is emerging unmistakably: Gen AI is not just enhancing work at Upwork; it is fundamentally redefining it.

About the Author

Dr. Gleb Tsipursky was named “Office Whisperer” by The New York Times for helping leaders overcome frustrations with hybrid work and Generative AI. He serves as the CEO of the future-of-work consultancy Disaster Avoidance Experts. Dr. Gleb wrote seven best-selling books, and his two most recent ones are Returning to the Office and Leading Hybrid and Remote Teams and ChatGPT for Leaders and Content Creators: Unlocking the Potential of Generative AI. His cutting-edge thought leadership was featured in over 650 articles in prominent venues such as Harvard Business Review, Fortune, and Fast Company. His expertise comes from over 20 years of consulting for Fortune 500 companies from Aflac to Xerox and over 15 years in academia as a behavioral scientist at UNC-Chapel Hill and Ohio State. A proud Ukrainian American, Dr. Gleb lives in Columbus, Ohio.

By Dr. Gleb Tsipursky

As companies rush to recalibrate workplace expectations in the wake of a more distributed workforce, one truth continues to crystallize: flexibility without leadership development is just chaos with good intentions. At ScienceSoft, a US-based software development company with an international presence, Head of PMO Pavel Ilyusenko understands that the success of hybrid and remote work hinges not only on strategy, but on skilled execution—particularly from the managers steering dispersed teams.

While much of the conversation surrounding flexible work revolves around where people work, Ilyusenko shifted the focus to how managers work in our interview. From his perspective, nurturing high performance in a flexible environment means cultivating a new breed of manager—one who mentors, guides, and supports teams without defaulting to micromanagement. In his words, “In remote work, the role of PM becomes the critical one.”

Building a Culture Without Walls

ScienceSoft’s approach to flexible work is far from tentative. The company leans into a hybrid model that empowers employees to work remotely when they need deep focus, or to come into the office for collaboration and meetings. Some team members, particularly those in nearshore and offshore locations, work fully remotely. The decision to adopt such a strategy is not about reacting to trends but rather aligning with the way software engineers actually do their best work.

“The hybrid model supports those needs by giving engineers control over their environment,” Ilyusenko explains. “It helps attract talent regardless of location and scale engineering teams more efficiently.” The result is a workforce that stretches across borders without losing cohesion or culture.

This cohesion, he emphasizes, is achieved through deliberate and frequent communication. The company uses familiar digital tools—Microsoft Teams, Asana, Jira, Confluence—but the real driver of success lies in how those tools are used. “It’s all about not the tools, but the approach that we cultivate within the teams,” he says. Team-building events, regular meetings, and a culture of open communication are baked into the daily workflow, not bolted on as an afterthought.

Mentoring as a Management Mandate

But flexible work, by its very nature, can blur accountability, fracture culture, and erode alignment if left unmanaged. That’s where leadership development becomes not a luxury but a necessity. ScienceSoft’s leadership understood early that success in a remote or hybrid model requires more than process—it demands mentoring.

“We pay more attention to mentoring and professional development of our project managers,” Ilyusenko says. Managers are not just expected to keep projects on track; they’re coached to lead without resorting to top-down oversight. This means building trust, giving autonomy, and staying closely attuned to both team performance and individual needs.

Mentorship isn’t left to chance. It is tracked, assessed, and fine-tuned through a combination of hard metrics and human feedback. Project outcomes such as delivery timelines, adherence to budget, and defect rates are monitored alongside client satisfaction scores like NPS and CSAT. But these metrics are enriched by softer indicators—direct feedback from team members about their managers, insights into leadership development, and even conversations with clients about improvement opportunities.

The result is a feedback loop that supports continuous growth, both for the manager and their team. Ilyusenko’s team doesn’t rely solely on performance data to evaluate effectiveness; they triangulate it with human insight. “We measure their success by gathering feedback from their teams and tracking their growth and leadership skills,” he says.

Turning Consistency into Competitive Advantage

One of the less obvious but more critical challenges in a hybrid environment is the consistency of execution across geographies and roles. ScienceSoft confronts this by standardizing its project management processes across the company, ensuring that no matter where employees are located, the way they approach and complete projects remains uniform.

This consistency creates what Ilyusenko calls “virtual rooms”—cohesive digital workspaces where teams can collaborate seamlessly. Whether an employee is logging in from a home office in Europe or joining a stand-up from a coworking space in North America, they’re operating within the same structure, guided by the same expectations, and supported by managers trained to lead under flexible conditions.

The emphasis on process discipline doesn’t constrain innovation—it protects it. By removing ambiguity from the workflow, ScienceSoft allows teams to focus on problem-solving and delivery rather than coordination and confusion.

The Steady Future of Flexible Work

While other organizations oscillate between in-office mandates and fully remote experiments, ScienceSoft’s path forward is measured and steady. “I would say that things will remain pretty much the same,” Ilyusenko reflects. “Expanding the workforce will require not only local people to be involved, but also people from all over the world.”

This is not inertia—it’s intentionality. By resisting the urge to overcorrect or chase the next big thing in workplace design, ScienceSoft anchors its remote and hybrid strategy in what works: flexibility, communication, mentoring, and consistency. Its bet is that a well-led team, empowered by choice and supported by strong processes, will outperform even the most closely monitored in-office staff.

As companies across sectors continue to navigate the complexity of flexible work, the lesson from ScienceSoft is clear: adaptability alone is not enough. To truly thrive, flexibility must be matched by mentorship. And that mentorship must begin at the top—with managers who are trained not just to manage tasks, but to develop people.

About the Author

Dr. Gleb Tsipursky was named “Office Whisperer” by The New York Times for helping leaders overcome frustrations with hybrid work and Generative AI. He serves as the CEO of the future-of-work consultancy Disaster Avoidance Experts. Dr. Gleb wrote seven best-selling books, and his two most recent ones are Returning to the Office and Leading Hybrid and Remote Teams and ChatGPT for Leaders and Content Creators: Unlocking the Potential of Generative AI. His cutting-edge thought leadership was featured in over 650 articles in prominent venues such as Harvard Business Review, Fortune, and Fast Company. His expertise comes from over 20 years of consulting for Fortune 500 companies from Aflac to Xerox and over 15 years in academia as a behavioral scientist at UNC-Chapel Hill and Ohio State. A proud Ukrainian American, Dr. Gleb lives in Columbus, Ohio.

By Dr. Gleb Tsipursky

The concept of Return to Office (RTO) has sparked significant debate and discord in the corporate world. While many companies strive to bring employees back to the office, the execution often falls short, resulting in dissatisfaction and inefficiency. To delve deeper into the reasons behind these failures, I had a conversation with Micah Remley, CEO of Robin Powered, a workplace management platform that helps around 2,000 companies implement hybrid work and flexible workplace strategies globally.

The Disconnect: Management vs. Employees

One of the primary reasons for RTO failures, according to Remley, is the fundamental disconnect between management and employees. Management often views returning to the office as a means to boost company performance and foster collaboration. However, employees, having experienced the efficiency of remote work, struggle to see the necessity of commuting back to an office environment that often mirrors their home setup.

This disconnect is exacerbated by the lack of clear communication and intentionality. “Employees don’t understand why they’re being called back to the office,” Remley notes. The common rationale that the office environment promotes better collaboration and productivity falls apart when the reality involves employees sitting in cubicles, similar to their home offices, with minimal face-to-face interaction.

The Cubicle Conundrum

Interestingly, cubicle sales have surged as companies attempt to recreate the quiet, private spaces of home offices within the workplace. However, this trend highlights a critical misalignment. The very essence of an office environment should be to facilitate interactions and collaborations that are challenging to achieve remotely. By making offices resemble home offices, companies strip away the unique benefits that an office setting should offer.

The data supports this misalignment. A recent report by the Survey of Working Arrangements and Attitudes (SWAA)  found that employees gain only about 80 minutes of additional face-to-face time per week when working from the office, which hardly justifies commuting time and effort. Thus, the expected collaborative advantage of being in the office is often not realized.

The Importance of Intentionality

Remley emphasizes that successful RTO strategies hinge on intentionality. This involves understanding and planning for the specific reasons employees should be in the office. Microsoft’s research on “moments that matter” identifies critical activities, such as the initiation of new projects or team-building exercises, that benefit significantly from in-person collaboration.

However, the challenge lies in predicting these moments. Research from Northwestern Kellogg School shows that 90% of workplace interactions happen at desks through spontaneous, everyday conversations. For these interactions to be fruitful, employees need to be in close proximity to their colleagues, a condition rarely met in current office setups where people are often dispersed.

The Failure of One-Size-Fits-All Approaches

Many companies falter by implementing rigid, top-down mandates, such as requiring employees to be in the office a set number of days per week without clear reasoning. This approach breeds resentment and fails to achieve the intended productivity boost. On the other hand, leaving the decision entirely to individual teams can result in inconsistency and a lack of coordinated effort.

Remley advocates for a balanced approach: creating a structured framework that outlines the company’s cultural and productivity goals while allowing teams the flexibility to adapt within this framework. This strategy ensures that employees understand the purpose behind the RTO policies and feel invested in their success.

Measuring Success: The Workplace Collaboration Score

To navigate the complexities of RTO, companies must measure the effectiveness of their policies. Surprisingly, most organizations lack proper metrics for evaluating the success of their RTO initiatives. Remley introduces the concept of a workplace collaboration score, which assesses three key components of in-person collaboration:

1. Occupancy: Tracking how occupied the office is and ensuring it aligns with collaboration goals.
2. Ad hoc Collaboration: Measuring the frequency and quality of spontaneous desk-side interactions.
3. Planned Collaboration: Evaluating the effectiveness of scheduled meetings and ensuring they foster the desired level of interaction.

For instance, Remley shares a revealing statistic from Robin’s data: 54% of meetings in conference rooms involve only one person on a video call. This indicates a significant misalignment, as these solitary meetings do not leverage the collaborative potential of the office.

Learning from Successful Companies

Companies that excel in their RTO strategies share common practices. They prioritize co-locating teams and ensuring they are in the office on the same days, fostering an environment conducive to collaboration. Additionally, they are intentional about where employees sit, promoting proximity to high performers to boost overall productivity.

These companies also empower employees by providing data and research to guide their decisions on when and how to come into the office. This approach not only enhances buy-in but also ensures that office time is spent effectively, fostering meaningful interactions and collaboration.

Conclusion: Crafting Intentional RTO Strategies

The path to successful RTO lies in intentionality, clear communication, and a balanced approach that combines structured frameworks with team-level flexibility – that’s what I advise my clients who ask me for how to optimize their flexible work plans. By understanding the unique benefits of in-person collaboration and designing office environments to enhance these interactions, companies can bridge the gap between management’s expectations and employees’ needs. As Micah Remley insightfully points out, the key is not just to bring employees back to the office but to create a purposeful, engaging, and productive workplace that justifies the return.

About the Author

Dr. Gleb Tsipursky was named “Office Whisperer” by The New York Times for helping leaders overcome frustrations with hybrid work and Generative AI. He serves as the CEO of the future-of-work consultancy Disaster Avoidance Experts. Dr. Gleb wrote seven best-selling books, and his two most recent ones are Returning to the Office and Leading Hybrid and Remote Teams and ChatGPT for Leaders and Content Creators: Unlocking the Potential of Generative AI. His cutting-edge thought leadership was featured in over 650 articles in prominent venues such as Harvard Business Review, Fortune, and Fast Company. His expertise comes from over 20 years of consulting for Fortune 500 companies from Aflac to Xerox and over 15 years in academia as a behavioral scientist at UNC-Chapel Hill and Ohio State. A proud Ukrainian American, Dr. Gleb lives in Columbus, Ohio.