Reflecting on Kleido: Lessons Learned in Building a Career Education Marketplace
In my previous blog post, Career Exposure: Seeing is Believing, I explored designing for intentional career exposure with Kleido, connecting students directly with professionals in a marketplace. As I moved from theory to practice, I encountered unexpected complexities and challenges that profoundly shaped my perspective on career education.
After bootstrapping and winding down Kleido, I reflected back on both its accomplishments and unresolved challenges. This post dives into those lessons, offering a behind-the-scenes look at how we tackled challenges like delivering authentic career advice, addressing professional skill gaps, and leveraging financial literacy. It highlights the innovative strategies we used to engage students, advisors, and schools, while also reflecting on what didn’t work and why.
Kleido’s journey reinforced the importance of meeting stakeholders where they are, aligning with their needs, and navigating the complexities of systemic barriers. These insights not only informed our approach but also revealed critical opportunities for innovation in career readiness. Whether you’re building similar programs or exploring ways to support the next generation, I hope these learnings offer a blueprint for meaningful impact.
Building a Marketplace Around Stakeholder Needs
Delivering Authentic Career Advice
Students today demand authenticity — they want relatable stories, not generic advice. Traditional career guidance often misses the mark, as it fails to align with students’ communication preferences, which now center on short-form content, text, and video. Ignoring these preferences risks losing their attention.
To deliver on the promise of authenticity, it’s critical to meet students where they are. At Kleido, we developed a question bank allowing students to personalize their inquiries, and we vetted advisors for more youth-focused experience. Advisors were trained to communicate effectively with today’s students, bridging generational gaps. This created a shared language between students and advisors, enabling more meaningful interactions. To ensure trust, we introduced short introductory videos from advisors, helping students feel more connected before their sessions. These steps fostered trust and engagement, making career exploration more authentic and accessible.
Teaching Professional Conduct
Many students lack foundational professional skills, such as punctuality, calendar management, and communication etiquette, especially early on in high school. These “soft skills” are often overlooked in traditional education but are critical for preparing successful professional relationships. When students miss appointments, show up late, or are unprepared for their sessions with advisors, it disrupts the value of the marketplace, risks harming their credibility, and discourages advisors from wanting to engage further, decreasing retention.
To bridge this gap, we implemented product features like automated reminders via email and text to help students remember their sessions and stay organized. Additionally, we created written guides that explained fundamental etiquette, such as the importance of punctuality, how to handle calendar invites, and the proper way to reschedule or communicate changes in plans. By incorporating these support tools, we guided students through their professional interactions from the very start during the first session, empowering them to build strong habits for ongoing career planning and professional growth.
Closing Financial Literacy Gaps
A significant gap in financial literacy emerged as we worked with students. Many were unaware of the lifestyle implications of different salary ranges, such as the difference between a $50K and $80K annual salary. They also struggled to understand concepts like the return on investment (ROI) for higher education and the extent of financial aid coverage. Without a solid understanding of these basics, students cannot make informed decisions about their education and career choices even after multiple exposures.
To address this gap, we guided students to ask critical questions about income expectations and ROI to professionals and parents, ensuring they had a realistic understanding of how their career choices could impact their future finances. Through partnerships with financial literacy organizations, we provided workshops in schools that helped students grasp key financial concepts and apply them to their individual circumstances. Other future plans included developing calculators to help students estimate first-year salary expectations. By empowering students with this knowledge, we aimed to give them a clearer picture of their financial future and the implications of their career and education choices.
Engaging Advisors Beyond Volunteering
Professionals who volunteered as advisors wanted more than just a chance to help; they desired meaningful interactions and a sense of impact. Many found traditional mentorship and volunteering models lacking in feedback, engagement, and community, making it challenging for them to feel connected to the process. Advisors wanted to know that their time was valuable and that their contributions were appreciated and impactful.
We recognize these needs of professionals and see them as an important part of the equation in delivering the most up-to-date and relevant career advice. We provided direct feedback from students, giving advisors insight into how their guidance made a difference. Even more, we want to unlock knowledge from the best — professionals who want to help and are normally too busy to volunteer. We met these needs by compensating advisors per session, with an option to donate their earnings, ensuring flexibility. This approach not only boosted advisor retention but also created a sustainable engagement model.
Supporting Parents as Career Navigators
The rapid evolution of technology and the job market have left many parents unable to provide relevant career advice to their children. The career advice they received in their youth often no longer applies in today’s competitive, tech-driven landscape. Many traditional job titles have evolved or disappeared, and new fields have emerged, leaving parents feeling unprepared to guide their children effectively.
As financial supporters for most of our students, parents needed to be convinced of the value of career services like Kleido for them and their children. To address this, we developed parent-specific dashboards and resources, including webinars and newsletters on emerging careers and skill trends. These resources helped parents understand the modern career landscape, the value of new and emerging job fields, and the importance of skills and networks relevant to today’s workforce. More importantly, educating parents built trust and encouraged them to invest in Kleido’s services. We were able to position them as supportive partners in their children’s career journeys, building trust and creating an environment in which both students and parents benefit.
Adapting to School Challenges
Working with schools presented its own set of rules and challenges. Schools are restricted by institutional standards and timelines, often with state and national supervision and compliance. Additionally, school counselors — ideally suited to facilitate career guidance — are overlooked, unprepared, and limited in their time and resources for career education. This created bottlenecks in implementing our services effectively within educational institutions.
To navigate this, we focused on teachers as champions for career readiness, aligning advisors to relevant classroom subjects. We offered in-school and afterschool integration by adapting our pathways and ensuring flexible scheduling. We partnered with financial literacy agencies and combined our curriculum of career and financial readiness to deliver value in future readiness. By being patient, adaptable, and responsive to each school’s unique needs, we made inroads, even within bureaucratic structures, and ensured that our program could support students across a variety of educational environments.
Navigating the Business Ecosystem
Direct-to-Consumer vs. School Sales
We initially prioritized direct-to-consumer sales, leveraging early successes to build credibility with schools. Selling directly to parents provided a faster path to revenue without the bureaucratic complexities of schools, especially as a founder without a formal pedagogical background. However, this strategy also required significant effort to convince individual families of the value of our services and involved competing for students’ out-of-school time, often packed with extracurriculars and other commitments. Alumni networks proved a reliable entry point for pilots and word-of-mouth growth. Alumni resonated with our value proposition, understanding the importance of social capital and networking as a boon for their children. We were able to recruit for our pilot through those networks, and successfully converted all our pilot users into paying customers. After proving the concept, we grew organically by meeting parents where they were — at local sports meets, in community events, and even hosting in-home gatherings to build trust and generate leads.
Selling to schools, on the other hand, offered a scalable pathway to reach students who might not otherwise have access to career resources. Schools could integrate Kleido into their curricula, ensuring consistent engagement without placing financial burdens on students. However, this approach came with its own challenges, as noted previously: Schools are relationship-driven, operate on strict budgets, and follow rigid timelines. My prior experience coaching at Cornell Tech provided valuable insights into how educators think, allowing us to position Kleido as a partner rather than a vendor. Additionally, we collaborated with existing vendors, which helped us navigate institutional hurdles and gain quicker adoption through pre-approved frameworks. We also focused on building teachers as ambassadors of career and future readiness and developing assets to make their voices heard. By balancing direct-to-consumer sales and school partnerships, we achieved more consistent growth, reduced seasonality, and created a more equitable reach across diverse demographics.
Non-Profit vs. For-Profit Business Model
Choosing a for-profit model for Kleido came with both advantages and challenges. As a for-profit, we aimed to build a self-sustaining business that wouldn’t rely on grants or donations. However, schools and other institutional partners often prefer to work with nonprofits, viewing them as more mission-aligned and less profit-driven. This dynamic limited our ability to partner more quickly with schools serving underprivileged students, who needed Kleido’s services the most but relied on institutional approval for access.
At one point, we considered creating a non-profit arm to align with schools’ expectations and extend our reach to underserved students. While this dual structure seemed promising, it would have introduced additional complexity to our operations. Instead, we focused on partnerships with established nonprofits. For example, collaborating with organizations like JobsFirstNYC allowed us to integrate proven frameworks and curricula while leveraging their existing relationships with schools and communities. These partnerships enabled us to scale faster, adapt to diverse needs, and extend our reach without compromising our for-profit business model.
Lessons from What Didn’t Work:
Educating Stakeholders Other Than Students
After nearly three years of building Kleido, we came to a tough realization: we were spending more time and resources educating stakeholders like parents and teachers than we were on the students themselves. Although we aimed to make our services accessible, navigating these gatekeepers are resource intensive. Schools often controlled access to students most in need, while parents needed significant persuasion to understand our value. This imbalance led to an unsustainable Customer Acquisition Cost (CAC) relative to the Lifetime Value (LTV) of our customers. Scaling these educational efforts was challenging given our limited funding. One potential solution could involve partnering with nonprofits specializing in training parents and teachers. This approach could reduce our CAC, making scaling more feasible.
Targeting Parents as Customers
Parents were an incredibly challenging target audience. While we found success through organic channels, such as community events and personal referrals, scaling these efforts required significant time and resources. Inorganic channels like digital ads or cold outreach proved less effective, as parents are often siloed, time-constrained, and inundated with competing priorities. If our founding team included parents or if we incorporated parent ambassadors into our founder-led sales efforts, we could significantly enhance our ability to connect with our target audience. Lived experience would provide a deeper understanding of parents’ unique challenges and priorities, enabling us to craft messaging and solutions that resonate on a more personal level. Similarly, parent ambassadors could serve as credible, relatable advocates, bridging the empathy gap and building trust within parent communities. Together, these approaches could make our outreach more effective, decrease our burn rate and increase engagement and conversion rates.
Supply-Driven Marketplace Dynamics
Kleido operated as a supply-driven marketplace, relying on high-quality professionals to attract student demand, which are sometimes hindered by their stakeholders and payability. While this approach ensured the availability of top-tier advisors, it introduced a constant “chicken-and-egg” problem. While we initially focused on the tech sector, narrowing our focus further to a niche like data analysts could drive the demand even more. To ensure growth, we could better monitor the ratio of students to advisors, continuously refine our vetting process to control our supply, and maintain this balancing act of quality and comprehensiveness. This approach could lead to a flywheel effect, where students not only learn but also become advisors themselves, bringing in more students in their network and fostering a self-sustaining growth cycle.
Despite achieving high Net Promoter Scores (NPS) and building a scalable process, Kleido ultimately struggled to reach product-market fit. Our growth was gaining traction but it was not stable and exponential, and our K-factor (viral growth coefficient) remained low. Given our high burn rate and limited funding, it became clear that continuing on our current trajectory would be financially unsustainable. To build a more viable path forward, we would need the time to pivot towards serving a high-end clientele or explore new market segments, such as adult learners. However, this shift would have diluted my mission to reach the students who need career exposure the most, especially with a financial model designed to alleviate, not impose, a burden on them.
This journey with Kleido has highlighted the complexities and challenges of building a career advice marketplace. I’ve gained a deeper understanding of the nuanced needs of students, the systemic barriers within schools, the critical importance of financial sustainability, and the transformative power of partnerships. This journey also taught me how to balance authenticity with scalability, adapt to diverse stakeholder needs, and iterate based on feedback. While Kleido’s path has been winding, it has reinforced my commitment in driving impactful solutions in education and career development.
If any of the above insights resonate, I would love to hear from you and explore further engagements!
