In industries like insurance, where change often comes slowly, insurance innovation is more than a buzzword—it’s a necessity. Few understand this better than Jared Kaplan, co-founder and CEO of Indigo, an AI-powered insurance technology platform revolutionizing medical malpractice coverage. With a career that spans fintech, real estate, and healthcare leadership, Kaplan has honed a powerful playbook that blends deep operational knowledge with bold innovation, embodying the traits of innovative leaders.
Kaplan recently talked with entrepreneur Adam Mendler, host of the podcast “Thirty Minute Mentors,” about his new company, and his leadership style and philosophy.
At the heart of Kaplan’s success is a commitment to effective leadership, clarity, and a bias toward action. Whether you’re a founder launching a startup or an executive running an established organization, his story is full of hard-earned lessons on scaling your business, empowering teams, and building something that lasts.
Kaplan believes that transparency, coupled with effective leadership skills, is one of the most underutilized tools in a leader’s arsenal. “Top talent craves autonomy, clarity of what success looks like, and ownership of achieving that success,” he told Mendler. By setting clear goals and continuously measuring progress, leaders create alignment and accountability. But they must also be open to feedback—especially the kind that challenges them.
“Constructive feedback is a gift, and you should reward those willing to push back thoughtfully,” Kaplan explains.
Achieving results requires collaborative efforts among team members, creating a shared vision, and fostering a supportive team environment.
His advice to leaders: Resist the temptation to say yes to everything. “Too many leaders rule by ‘and’ instead of ‘or’. I have found maniacal focus on a handful of initiatives creates better outcomes vs. trying to do everything.”
Kaplan’s career might span elite firms and startup ventures, but his drive was forged early. Growing up in the Midwest with an identical twin instilled a spirit of healthy competition and grit. “Going through my childhood and teenage years with someone to healthily compete with allowed me to maximize every ounce of my academic and athletic potential at a young age,” he recalls.
Kaplan's journey has been marked by adapting to different challenges presented by various teams, projects, and situations.
That early momentum carried him to the University of Michigan’s Ross School of Business and then into investment banking at Goldman Sachs. Later, at Accretive—a firm known for incubating new ventures—Kaplan began to envision a different path: entrepreneurship.
One of Kaplan’s signature philosophies is deceptively simple: “Become a tree expert.” In other words, before trying to scale, know your area of the business inside and out.
“When you’re really in it while building and running a business, you may not be able to see the forest from the trees, but if you master your area of expertise, you earn the right to elevate by being a tree expert and become mission critical to the company,” Kaplan says.
This attention to detail and focus on the fundamentals helped him launch Insureon, which became the fastest-growing agency in property and casualty insurance before it was acquired by Hub International and Bold Penguin. Later, he led fintech firms OppFi (which went public in 2021) and Cadre, a venture-backed commercial real estate platform, where new ideas were developed to drive success.
For Kaplan, the formula for scaling your business begins with great people and ruthless prioritization. “Sustainable business growth is driven by attracting and retaining top talent, clear prioritization of the company’s top initiatives at every stage of growth, and leading with transparency,” he says.
Achieving these results is closely tied to aligning efforts with the organization's objectives and organizational goals.
Leaders must set high expectations, but they should also know how to motivate without overwhelming. Kaplan advocates for what he calls “comfortably uncomfortable goals”—objectives that stretch people but remain achievable. Unrealistic targets, he warns, are demoralizing and ultimately counterproductive.
As a technology entrepreneur, Kaplan has consistently bet on industries where digital transformation is lagging—but inevitable. Indigo’s use of artificial intelligence in medical malpractice coverage is a prime example of insurance innovation with real-world value, adapting to market needs by leveraging technology and innovation.
“Even though AI is nearly everywhere today, we are underestimating the power of AI,” Kaplan notes. “Technology should be integrated across the entire organization, not just within one or two departments.”
Startups, he says, often have a distinct advantage: they aren’t burdened by outdated infrastructure or cost structures. That agility makes it easier to embed insurance technology from the ground up and drive faster, more meaningful results.
For example, Indigo’s AI-driven approach not only streamlines the insurance application process but also ensures that physicians receive coverage tailored to their specific risk profiles. By analyzing thousands of data points, Indigo offers individualized pricing, rewarding doctors who practice good medicine with potential premium savings.
Moreover, Indigo’s commitment to rigorous defense means that physicians can practice with confidence, knowing they have a dedicated team ready to protect them in times of need. The company’s financial strength, underscored by an A- (Excellent) rating from AM Best, further assures clients of its reliability and stability.
In the insurance industry, decision making and critical thinking are indispensable leadership skills. Effective leaders must swiftly analyze complex data, discern patterns, and make informed decisions. The ability to think critically is crucial in navigating the ever-changing landscape of the insurance sector, where new technologies and market trends can emerge at a rapid pace.
Good leaders must think creatively and develop innovative solutions to complex problems. By honing strong critical thinking skills, insurance leaders can drive business success and maintain a competitive edge.
If there’s one quality Kaplan returns to again and again regarding leadership qualities, it’s humility. Leaders, he believes, must never stop learning—and that often means listening more than talking.
Professional development is crucial for enhancing leadership skills and fostering personal growth within teams, emphasizing the importance of continuous learning and skill improvement.
“Many leaders have a bad habit of becoming ‘know-it-alls’ over time where they stop listening to their teams and predispose a solution because it worked before,” he says. “If you hire top talent, they are always closer to the actual work, and their word is typically gold.”
He encourages leaders to reflect on their own past and remember what it was like to be on the other side of the org chart. “Act the way you wish you’d been treated in those moments,” he adds.
For founders and executives alike, Kaplan emphasizes the need to create real, measurable value. “You need to develop a product or business that quantifiably creates value for the customer above that customer’s next best alternative by wisely allocating resources,” he says.
He cautions against sinking money into broad, traditional brand campaigns—especially early on. Instead, focus on high-impact, lower-cost levers like SEO, customer testimonials, speaking at industry events, and building a personal brand on platforms like LinkedIn.
“Test, test, and test again,” Kaplan advises. “Once you’ve determined what works best for your business, double down.”
Kaplan’s playbook for founders and civic leaders centers around three guiding principles, he told Mendler:
These habits, combined with humility and strategic vision, form the foundation of Kaplan’s approach to effective leadership. Real-world examples of renowned leaders, such as Steve Jobs and Bill Gates, highlight how examining the experiences and behaviors of successful individuals can develop effective leadership skills.
Kaplan’s final message speaks to his core identity as a technology entrepreneur: find legacy systems that are ripe for disruption and bring them into the future. “Though I consider myself a technology entrepreneur and have worked across a variety of different industries, I have been able to leverage a similar playbook each time by seeking out ‘old school’ industries ripe for disruption from ‘new school’ technologies,” he says.
Kaplan’s vision for Indigo extends beyond just offering superior insurance products. He aims to foster a supportive environment for healthcare professionals, ensuring they can focus on delivering quality care without the added stress of cumbersome insurance processes. By integrating advanced technology with a deep understanding of the medical field, Indigo is poised to set a new standard in medical malpractice insurance.
In a rapidly evolving healthcare landscape, companies like Indigo exemplify how technological innovation can lead to more efficient and effective solutions. As Kaplan says, “At the end of the day, we want to take the hassle out of buying a required line of insurance for your business so you can focus on much more important things like life and death decisions.”
In an era where innovation is the differentiator, Kaplan proves that blending traditional business fundamentals with forward-thinking tools isn’t just smart—it’s essential for generating innovative ideas.
The insurance industry is currently navigating a landscape filled with emerging trends and challenges, such as the rise of insurtech, evolving customer expectations, and increasing regulatory requirements. Effective leaders must adeptly manage these challenges while identifying opportunities for growth and innovation.
Leveraging new technologies like AI, cloud computing, and open APIs, insurance companies can streamline operations, enhance customer satisfaction, and reduce costs. However, leaders must also be vigilant about potential risks, including data security and regulatory compliance, to ensure sustainable success.
Navigating change and uncertainty is a critical leadership skill in the insurance industry. With the advent of new technologies and shifting market trends, insurance companies must adapt swiftly to stay competitive. Effective leaders must develop a clear vision and strategy for their organization, communicate effectively with employees and customers, and drive innovation and growth.
By cultivating strong leadership skills such as self-awareness, emotional intelligence, and strategic thinking, insurance leaders can successfully navigate change and uncertainty, driving their organizations toward success.
In conclusion, leadership skills are essential for success in the insurance industry. Effective leaders must possess a unique set of skills, including strategic thinking, relationship building, and critical thinking. By developing these skills and staying ahead of industry trends and challenges, insurance leaders can drive business success and achieve future growth.
As Steve Jobs once said, “Innovation distinguishes between a leader and a follower.” In the insurance industry, innovation and leadership are intertwined, and companies that prioritize these values will be best positioned for success in the years to come.
By following the examples of successful leaders like Bill Gates and studying the latest research and trends, insurance leaders can develop the skills and knowledge needed to achieve their goals and drive their organizations forward.
For medical professionals, the message is clear: the financial stakes are growing. Having robust malpractice insurance is a critical responsibility of professional practice. To that point, do you know how much you are paying for medical malpractice insurance for your practice?
Clearly defining expected outcomes in innovation projects can facilitate leadership support, which is essential to secure funding for these initiatives.
Indigo offers excellent medical malpractice insurance options for healthcare providers. They understand the unique risks doctors face and offer coverage that suits various specialties. Whether you’re new or experienced, Indigo’s policies protect you from the financial risks of malpractice lawsuits.
Reach out to our team members and secure the right medical malpractice insurance to protect yourself.
Image by Igor Kutyaev from iStock.
