A.J. Thomas, the CEO of Troublemaker Lab and Founder and General Partner of Good Trouble Ventures, where she helps extraordinary founders build enduring companies through coaching, strategy, and mindful innovation. She ran global talent and human experience design groups at X—the "moonshot factory" known as Google X—and served as CXO-in-residence at A.Team.
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1. Connecting Strategy to the Frontline: Why Employee Experience Drives Business Results
Nicole shares the story behind building FirstUp and how she helped shape the digital employee experience category. The conversation centers on a simple but often overlooked reality: companies cannot execute strategy if their people do not understand it, feel connected to it, or see how it applies to their daily work.
A major focus of the discussion is frontline workers. Nicole explains that around 80 percent of the global workforce works in roles like retail, healthcare, manufacturing, hospitality, and frontline financial services. Historically, these employees have been the hardest to reach, often relying on outdated methods such as bulletin boards, paper notices, or messages passed through layers of managers. These approaches break down quickly and leave employees disconnected.
Nicole and Alex talk about how FirstUp approached this problem by taking ideas from consumer marketing and applying them to employee communications. Just as brands personalize messages for customers through mobile and digital channels, companies can use similar techniques to deliver timely, relevant information to employees, especially those on the frontline. This includes everything from operational updates and safety information to culture and engagement messages.
The problem is most acute there because a lot of companies, before us, were literally trying to talk to their employees through layers and layers of managers and even telephone trees. (Nicole Alvino)
2. Bringing Marketing Thinking Into Employee Communications
Alex starts by comparing today’s customer marketing with traditional employee experience. While marketing delivers personalized messages across channels and moments, employee communications have often looked like static portals: one login, one format, outdated content, and the same experience for everyone. Nicole agrees and points out that almost no one truly liked their old intranet systems, which made it clear there was a real problem to solve.
A key theme in the conversation is the lack of technology built specifically for internal communications. Nicole explains that marketing, sales, and HR were transformed once they got dedicated platforms that allowed teams to run campaigns, measure results, and prove impact. Internal communications, however, had long been left behind without tools to show what worked and what didn’t.
They talk about how applying a campaign mindset to employee communications changes everything. Instead of just posting information, companies can measure who reads messages, who completes training, and how engagement links to real outcomes. Nicole gives the example of safety communications, where companies can track engagement by location and see safety incidents drop as a result.
There was also no denying there was no good way for companies to reach frontline workers—whether that person was driving a truck, interacting with a patient or guest, or working on a manufacturing line. (Nicole Alvino)
3. From Top-Down Messages to Personal Connection at Work
Nicole explains that early customers like Boeing, Dow, and Hilton all faced the same problem: they had no effective way to reach most of their workforce, especially frontline employees. For leaders responsible for culture and strategy, this gap was impossible to ignore. If the majority of employees are disconnected, it becomes very hard to move the company forward, build trust, or create a shared sense of purpose.
Alex adds historical perspective, describing what happens in highly top-down systems where communication flows in one direction and employees feel no ownership or alignment. Both agree that large organizations often drift into smaller versions of this problem as they grow.
The conversation then shifts to how workforce expectations are changing. Nicole points out that Gen Z will make up a large share of the workforce in just a few years. This generation is digital-first, expects interaction rather than one-way messaging, and wants to feel connected to something meaningful. At the same time, companies still employ multiple generations, each with different habits, preferences, and learning styles.
Alex highlights the complexity of this challenge: companies can’t simply redesign everything for one generation. Messages still need to reach senior leaders, frontline workers, and everyone in between, often in different formats and levels of depth.
Nicole explains that the solution lies in meeting people where they are. That means communicating in ways that match individual preferences, roles, life stages, and moments of need. She uses employee benefits as a clear example. Many benefits go unused not because they lack value, but because employees don’t receive the right information at the right time.
You need to meet people where they are—physically, digitally, in their language, their context, their career stage, and their life stage. (Nicole Alvino)
4. Why Big Companies Need Better Ways to Talk to Their People
Alex starts by breaking down two parts of effective communication at work:
• delivering accurate, relevant, personalized information, and
• packaging it as a story people care about and can act on.
When both are done well, employees not only receive information but also understand it, learn from it, and eventually change how they work.
Nicole shares what went into building a platform that supports this at scale. From day one, FirstUp decided to sell to large organizations. That meant longer sales cycles and more complexity, but the problem they were solving simply didn’t exist in small companies. Once a company has thousands of employees spread across roles, locations, and time zones, communication becomes messy fast. If everything is treated as one-size-fits-all, employees tune out, and important messages get lost.
Another hurdle was stakeholder complexity. Internal communications teams often work under HR, and HR teams often work with IT, while executive approval may come from the CEO or CFO. Nicole talks about how buying decisions in these environments require multiple champions and clear ROI. Sometimes the CEO gets directly involved because they personally want a better way to talk to the workforce, like in the case of Tesco. Nicole argues that this is ultimately a CEO-level problem: if strategy needs people, then communication needs to work.
Alex also points out the pressure higher stakes bring. In large companies, internal communications include CEO messages, organizational changes, safety information, and cultural alignment. If something breaks, it’s a real issue. Nicole explains that the company had to build for reliability, personalization, and global scale—while also supporting different types of employees, devices, and levels of digital comfort.
Family offices don’t have quarterly reporting requirements. They have the flexibility to invest in areas they’re passionate about and that align with their investment thesis. They also have patient capital—and patient capital is exactly what’s needed in domains like deep science. (Nicole Alvino)
5. How Tech Leaders Are Rethinking the Intranet and Employee Experience
Nicole explains that intranets used to belong almost entirely to IT. Today, CIOs still play a major role, especially as companies try to consolidate software after years of heavy spend during COVID. CIOs are now asked to reduce costs, make systems work together, and invest in AI, all while improving how employees experience work from hiring to retirement.
Some CIOs want to build parts of the employee experience themselves and plug in specialized platforms where needed. Others still insist on owning the portal and sticking with tools like Microsoft or ServiceNow. In both cases, communication platforms like FirstUp have to integrate, enhance what already exists, and offer capabilities that traditional productivity tools don’t—especially around engagement and personalization.
The conversation also highlights why this topic connects directly to CEOs. Tools that help companies communicate strategy, culture, and change ultimately serve executive priorities. When CEOs care about connecting with employees—not just sending updates but actually involving people—technology becomes a strategic lever, not just infrastructure.
Alex then turns the conversation to Nicole’s personal journey as a founder. She talks about the challenge and responsibility of “using your own product” when you build communications software. For her, the most rewarding part of building FirstUp was the people: helping employees grow, develop new skills, move into new roles, and feel proud of their work.
At the same time, she acknowledges the hard reality that companies change over time and not everyone stays forever. Different stages require different people, and part of leadership is helping individuals find the right place for themselves—whether inside or outside the company.
The hardest and most rewarding part of building a company is the people. Connecting with them and bringing them along. (Nicole Alvino)
6. How Early Lessons, Frontline Workers, and Personal Priorities Shaped a Founder’s Path
Nicole shares that her time at Enron was intense. She worked in structured finance, and several of her managers eventually went to jail. Two of the people who wrote her business school recommendations even ended up there. That experience made her question whether she wanted to stay in business at all. She took time off to travel, reflect, and reset, and realized that she genuinely loved building things and making an impact—so she decided to return to business, but on her own terms.
One takeaway from that period was that she would only build companies where she could influence the culture, ethics, and values directly, so she wouldn’t repeat an Enron-style situation. She wanted to create environments where people felt connected, supported, and proud of their work.
After business school, she didn’t immediately build a tech company. Her first venture was a spa business, and that chapter taught her the importance of frontline employees. The customer experience depended entirely on the workers providing services—just as in many industries where frontline workers make up the bulk of the workforce. That led her to the insight that eventually shaped FirstUp: large companies needed a better way to communicate with and support the people doing the work—not just those behind desks.
Alex then shifts to a more personal question. He notes that Nicole has a calm, positive energy and asks what her secret is, especially given the demands of being a CEO, parent, and leader. Nicole explains that she doesn’t believe in strict balance; instead, she looks for peace and presence. She has non-negotiables—like never traveling on her kids’ birthdays—and has accepted that no one can be a “ten” in every dimension every day. Meditation helps her stay grounded, and knowing her priorities keeps her centered as both a leader and a parent.
There’s no such thing as balance. There’s no work-life balance. I’m a big “and” person. There is peace. There are moments of peace. (Nicole Alvino)
7. Leadership, Presence, and Purpose
Alex asked how she brings that mindset into the workplace, especially in environments focused on growth and performance. Nicole said the key is to talk about these things openly and normalize them. She pointed out that younger generations expect leaders to be real and transparent, not polished robots. For her, authenticity also means adding humor, fun, and human connection—like asking customers to share a quirky fact about themselves. It breaks the ice, creates deeper relationships, and makes business interactions feel less transactional.
Toward the end, Alex asked what advice Nicole would give her younger self when starting FirstUp. She said she would tell herself to trust her instincts and not overthink. When she ignored her gut, she usually regretted it. She also shared a favorite quote: “Don’t sweat the small stuff—and it’s all small stuff.” Stepping back and keeping perspective helps during both the highs and the lows.
Alex closed by asking where listeners can learn more about Nicole and FirstUp. She pointed people to LinkedIn, the FirstUp website, and her email, and encouraged communication leaders to reach out and connect.
I would say always trust my instinct—trust my gut. I can look back at times when I didn’t and made decisions that went against what I knew, and invariably they didn’t turn out the way I wanted. (Nicole Alvino)
Check the episode's Transcript (AI-generated) HERE.