Foster a Culture of Continuous Improvement: Interview with Didi Azaria, CEO of Workiz
I recently went one-on-one with Didi Azaria, CEO of Workiz.
Adam: How did you become the CEO of Workiz? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?
Didi: Before joining Workiz in 2018, I co-founded Sisense (2004), a business analytics startup that achieved unicorn status (> 100M ARR). This experience provided me with deep insights into building and scaling tech companies like Uber, Wix, and Target, how they analyze their data and make business decisions. Transitioning to Workiz, I leveraged these learnings to address challenges in the field service industry, particularly for professionals like locksmiths, plumbers, and HVAC technicians.
My path to becoming a successful CEO hasn't followed a straight line. My entrepreneurial journey began long before my arrival at Workiz in 2018. My drive to build and create was evident when I co-founded Sisense, a data analytics platform that would go on to transform how businesses interpret and utilize their data.
At Sisense, I witnessed firsthand the challenges of scaling a tech startup from its early stages to becoming a unicorn company with over $100 million in annual recurring revenue. This experience was invaluable, providing me with a comprehensive understanding of what it takes to build a successful tech company from the ground up.
Building Sisense taught me that success isn't just about having cutting-edge technology. It's about understanding your customers' pain points and creating solutions that address their specific needs.
Perhaps most critically, my time at Sisense allowed me to observe how major companies across various industries handle their data analytics needs. This insight would prove crucial when I later identified the opportunity to bring similar technological advantages to the traditionally underserved field service sector.
When the opportunity at Workiz presented itself, I recognized a chance to apply my experience in a new context—helping small to medium-sized field service businesses compete in an increasingly digital marketplace.
The field service industry was ripe for digital transformation. These professionals—plumbers, locksmiths, HVAC technicians—are incredibly skilled at their trades but often lack the technological tools to optimize their businesses. I saw an opportunity to change that.
Adam: What are the key steps to growing and scaling your business?
Didi: Focusing on understanding and addressing the specific needs of our target audience has been crucial. By tailoring our solutions to the unique challenges of field service professionals, we've been able to drive growth and scalability.
I believe the foundation of business growth begins with deep customer understanding. At Workiz, this meant immersing myself in the day-to-day realities of field service professionals to identify their most pressing challenges.
We spent countless hours shadowing service professionals, observing their workflows, and identifying the friction points in their daily operations. This hands-on approach gave us insights that no market research report could provide.
This customer-centric approach revealed that field service professionals faced unique challenges: managing unpredictable schedules, coordinating technicians across multiple locations, providing accurate estimates onsite, and handling payment processing efficiently. These insights directly informed our product development roadmap at Workiz.
I've learned that scaling requires more than just growing your customer base—it necessitates building systems that can accommodate growth without diminishing quality or customer experience.
As we scaled, we implemented advanced automation to handle routine processes while ensuring our customer support team maintained the personal touch that field service professionals value. This balance between technological efficiency and human connection has been critical to our sustained growth.
Another key aspect of our scaling strategy at Workiz has been developing a platform that grows with our customers.
I designed our solution to be valuable for the lone technician just starting out, but also robust enough to support businesses as they expand to multiple technicians and locations. This scalability within our own product has facilitated our customers' growth while simultaneously driving our own.
Adam: What is your best advice on building, leading, and managing teams?
Didi: Emphasizing persistence, resistance, and self-awareness is vital. Great leaders are persistent in their pursuit of success and self-aware, recognizing their strengths and areas for growth.I believe effective leadership begins with self-understanding. I regularly assess my own performance, seeking feedback from team members at all levels of the organization.
"Leadership isn't about having all the answers. It's about assembling a team with complementary strengths and creating an environment where they can thrive.
This philosophy is evident in how I structured the leadership team at Workiz, bringing together individuals with diverse expertise spanning technology development, field service operations, customer success, and business scaling.
Building on my emphasis on persistence, I consider resilience a non-negotiable quality for both leaders and their teams.
In the startup world, setbacks are inevitable. The difference between successful and unsuccessful companies often comes down to how they respond to these challenges. Do they learn, adapt, and persevere, or do they become demoralized and lose focus?
To foster this resilience, I've implemented several practices at Workiz:
Celebrating failures as learning opportunities
Establishing clear, meaningful metrics for success
Creating transparent communication channels across all levels of the organization
Encouraging cross-functional collaboration to solve complex problems
Providing continuous growth opportunities for team members
Building a great team isn't just about hiring the right people—though that's certainly important. It's about creating a culture where talented people want to stay, grow, and do their best work.
Adam: What are the most important trends in technology that leaders should be aware of and understand? What should they understand about them?
Didi: AI is transforming various industries, including field services. Leaders should understand how AI can enhance efficiency, improve customer experiences, and drive profitability. Embracing AI as a tool for enhancing productivity is essential for staying competitive and surviving in today's market.
I firmly believe we've entered a new technological era where AI will separate industry leaders from those left behind. I've found that modern leaders must develop a working understanding of AI capabilities, limitations, and implementation strategies.
The AI revolution isn't coming—it's already here. But many businesses, especially in traditional industries like field services, are just beginning to recognize its potential.
For field service businesses specifically, I see several AI applications with immediate practical value:
Intelligent scheduling algorithms that optimize technician routes and appointment times
Predictive analytics that forecast service demand and identify potential equipment failures before they occur
Natural language processing for improved customer interactions and service documentation
Automated follow-ups and personalized communication based on customer history
Visual recognition tools that can help technicians identify parts and equipment
What leaders need to understand about AI is that it's not about replacing human workers—it's about augmenting their capabilities. AI can handle routine tasks, process vast amounts of data, and identify patterns that humans might miss, freeing up technicians and office staff to focus on high-value work that requires human judgment and expertise.
I also stress the importance of implementing AI in ways that align with specific business objectives rather than adopting technology for its own sake.
Before implementing any AI solution, I always ask myself: What specific business problem am I trying to solve? How will this technology improve our customer experience or operational efficiency? What metrics will demonstrate success?
Adam: What do you believe are the defining qualities of an effective leader?
Didi: Persistence and self-awareness are defining qualities of effective leaders. These traits enable leaders to navigate complexities, inspire their teams, and create a lasting impact within their organizations.
I believe leadership transcends management techniques or business strategies—it's fundamentally about character and personal qualities that inspire others to achieve their best.
Persistence stands at the core of my leadership philosophy. I've found that meaningful success rarely comes quickly or easily, particularly in the technology sector where innovation often involves multiple iterations and failures before breakthroughs.
True persistence isn't just about working hard. It's about maintaining clarity of vision and purpose even when faced with obstacles that would cause others to abandon their path.
Equally important in my leadership framework is self-awareness—the ability to accurately assess one's own strengths, weaknesses, emotional states, and impact on others.
Self-aware leaders understand when to trust their instincts and when to seek guidance. They recognize that leadership isn't about being the smartest person in the room—it's about creating an environment where collective intelligence can flourish.
I've noticed that these qualities are particularly relevant in today's rapidly evolving business landscape, where technological advances and market shifts can quickly render traditional business models obsolete.
Leaders who combine persistence with self-awareness can navigate uncertainty while remaining open to new information that might necessitate a change in direction. I persevere in pursuit of my vision while remaining flexible about the path to achieve it.
Adam: How can leaders and aspiring leaders take their leadership skills to the next level?
Didi: Embracing AI and other emerging technologies can significantly enhance leadership capabilities. Leaders should focus on practical and impactful AI applications, tailoring solutions that truly fit their industry and organizational needs.
I believe that leadership development in the modern era must incorporate technological fluency alongside traditional leadership skills. I advocate for aspiring leaders to develop what I call "augmented leadership"—combining human qualities like empathy and vision with technological tools that expand decision-making capabilities.
Tomorrow's leaders need to understand technology not just as a set of tools, but as an extension of their leadership capabilities. This doesn't mean every leader needs to become a programmer, but they should understand enough about emerging technologies to recognize opportunities for implementation within their organization.
Beyond technological adaptation, I emphasize several practices for leadership development:
Seeking diverse perspectives and experiences outside one's industry or functional area
Developing mentorship relationships—both as mentor and mentee
Creating deliberate learning routines, including reading, reflection, and skill development
Building networks that provide honest feedback and challenging viewpoints
Practicing mindfulness to enhance self-awareness and emotional regulation
Leadership development is never complete. The best leaders maintain a growth mindset throughout their careers, constantly seeking new challenges that stretch their capabilities.
Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?
Didi: 1. Embrace AI and Automation: Leverage technology to increase efficiency and profitability. 2. Understand Your Industry's Specific Needs: Tailor solutions to address the unique challenges of your target audience. 3. Foster a Culture of Continuous Improvement: Encourage persistence and self-awareness within your teams to drive sustained growth.
Expanding on these three pillars of leadership, I offer practical implementation strategies for each:
1. Embracing AI and Automation
I recommend starting by identifying repetitive, time-consuming tasks within your organization. These are prime candidates for automation or AI enhancement.
I suggest beginning with small-scale implementations that deliver quick wins before tackling more complex applications. This approach builds organizational confidence in technological solutions while providing valuable learning experiences.
I've learned that successful technology implementation is as much about change management as it is about the technology itself. Invest time in training, clear communication about objectives, and celebrating early successes.
2. Understanding Industry-Specific Needs
I recommend a structured approach to gaining industry insights:
I find it valuable to establish regular customer feedback channels—both formal and informal. I supplement this with competitor analysis, industry trend research, and ongoing dialogue with frontline employees who interact directly with customers.
I emphasize the importance of developing solutions that address the specific context in which customers operate rather than generic offerings that partially meet many different needs.
At Workiz, I discovered that field service professionals face unique challenges around scheduling, dispatching, and on-site payment processing. By focusing intensely on these specific needs rather than creating a generic business management platform, we've been able to deliver significantly more value.
3. Fostering Continuous Improvement
I believe creating a culture of continuous improvement requires both structural support and personal modeling.
As a leader, I need to demonstrate that learning and growth are valued by sharing my own development journey. When team members see leaders acknowledging their mistakes and actively working to improve, it creates psychological safety for everyone to do the same.
Structurally, I recommend implementing:
Regular retrospective meetings that focus on learning rather than blame
Performance metrics that include growth and development, not just outcomes
Resources for personal and professional development
Recognition for innovative thinking, even when ideas don't succeed
Cross-training opportunities that broaden skills and perspective
Adam: What are your best tips on the topics of sales, marketing, and branding?
Didi: Building a strong brand involves understanding your customers' needs and delivering tailored solutions. Effective marketing and sales strategies should focus on demonstrating how your product or service addresses specific pain points, thereby building trust and credibility with your audience.
I approach marketing and sales as natural extensions of the customer-centric philosophy that drives product development at Workiz.
I believe the most effective marketing isn't about clever messaging or attention-grabbing tactics. It's about clearly communicating how your solution solves real problems for your customers.
For business-to-business sales, particularly in specialized industries like field services, I emphasize the importance of educational content that helps potential customers recognize problems they might not have fully articulated.
Many of our customers knew they were struggling with scheduling inefficiencies or payment delays, but they didn't necessarily connect these challenges to their technology limitations. Our most effective marketing helps them make this connection and understand how digital tools can address these pain points.
When it comes to branding, I believe authenticity trumps perfection. I advocate for brands to embrace their unique identity and communicate it consistently across all touchpoints.
At Workiz, we don't pretend to be all things to all businesses. We're specifically designed for field service professionals, and our branding reflects this focused expertise.
This authenticity extends to customer relationships as well. I encourage businesses to be transparent about both capabilities and limitations, building trust through honesty rather than overpromising.
Adam: What is the single best piece of advice you have ever received?
Didi: The most impactful advice I've received is to focus on a smaller niche rather than targeting the largest one. This approach allows for a more tailored offering, addressing specific customer needs and building a loyal client base. By concentrating on a defined segment, businesses can differentiate themselves and establish a strong market presence.
This principle of focused strategy has guided many of my business decisions, including the positioning of Workiz within the broader business software market.
When we launched Workiz, I could have attempted to compete as a general business management platform. Instead, I chose to focus exclusively on field service businesses, becoming experts in their specific workflows and challenges.
This focused approach allowed us to develop deep expertise and tailored features that generalist platforms couldn't match. By thoroughly understanding the unique needs of field service professionals, we created solutions specifically designed for their workflows, terminology, and business models.
The conventional wisdom often pushes entrepreneurs to target the largest possible market. But I've found that starting with a well-defined niche allows you to build something truly excellent for a specific audience, rather than something mediocre for everyone.
This strategy has practical implications beyond product development—it influences marketing efficiency, customer acquisition costs, and retention rates.
When I focus on a specific niche, my marketing can speak directly to their pain points in their language. This not only improves conversion rates but also attracts customers who are likely to find genuine value in your offering and remain loyal over time.
Adam: Is there anything else you would like to share?
Didi: As we look ahead, our focus is on practical and impactful AI applications. By collaborating closely with our customers, we aim to tailor AI solutions that truly fit the field service industry, revolutionizing how professionals work and succeed.
I envision a future where AI-powered tools democratize access to advanced business capabilities, allowing small and medium-sized field service businesses to compete effectively with larger corporations.
The field service industry has traditionally been dominated by small businesses—skilled tradespeople who excel at their craft but often lack the technological resources of larger companies. I believe AI has the potential to level this playing field, giving these businesses access to capabilities that were previously available only to enterprises with substantial IT budgets.
Specifically, I see AI transforming field services in several key areas:
Predictive scheduling that optimizes technician routes while accounting for traffic patterns, weather conditions, and historical service duration data
Smart inventory management that anticipates parts needs based on job types and customer history
Automated customer communication that provides timely updates throughout the service process
Voice-enabled documentation that allows technicians to record notes and details hands-free while working
Intelligent pricing recommendations based on job complexity, market conditions, and customer history
The most exciting aspect of these technological advancements is that they don't replace the human element that's so crucial in field services. Instead, they enhance it by removing administrative burdens and allowing technicians to focus on what they do best—solving problems and delivering excellent service.
As we continue to develop these technologies at Workiz, I remain committed to the collaborative approach that has guided our company's growth thus far.
I believe the future of field service technology won't be created in isolation by software developers. It will emerge through ongoing dialogue between technology providers and the professionals who use these tools every day. This partnership approach is how we'll develop solutions that truly transform the industry.
Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one-on-one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders - for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.
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