Learning and development leaders face a stubborn paradox: They must focus on individualized development paths, but most work happens in teams. Employees take courses, complete assessments, and build skills in isolation, but then must apply them collaboratively. Training programs measure individual progress while teams often struggle with dysfunction or suboptimal performance.
Brandon Hall Group™ recently connected with Darrin Murriner, CEO and Co-founder of Cloverleaf, to understand how they’re addressing this gap. Based in Cincinnati and serving over 45,000 teams globally, Cloverleaf has achieved impressive growth — landing on the Inc. 5000 list for three consecutive years with 450%+ growth rates and securing $7.3 million in Series A extension funding earlier this year. Their approach centers on a premise most competitors miss: team development requires fundamentally different tools than individual development.
This briefing reinforced patterns we’re observing across the AI coaching landscape through our Institute™ and the technology evaluation and selection work with corporate clients. The market has shifted from education to evaluation, and buyers are now running structured selection processes with specific feature requirements.
Where AI Coaching Stands Today
The AI coaching market has matured rapidly over the past year. What began as a category requiring extensive buyer education has evolved into a recognized solution space, with L&D and talent management leaders actively seeking specific features like role-playing and real-time feedback capabilities. Our research shows that half of organizations remain uncertain about AI adoption and progression, creating both pressure and opportunity for coaching providers.
Through our ongoing analyst briefings with solution providers, we’ve mapped the competitive landscape, which reveals a divide in how providers approach the problem.
- BetterUp pioneered digital coaching over a decade ago and launched its AI offering, BetterUp Grow, in January 2025. The platform focuses primarily on individual development with role-specific guidance.
- CoachHub AIMY launched in early 2025 and now serves 60+ global enterprise clients. The platform, which began with a European focus, provides 24/7 multilingual support across 80+ languages and was built specifically to complement their human coaching network of 3,500+ certified coaches.
- Valence entered the market in early 2023 and raised $50M in Series B funding in September 2025. Their AI coach, Nadia, customizes deployments to company culture and leadership frameworks and focuses on manager effectiveness, but remains individually oriented in coaching approach.
Each competitor brings meaningful innovation to AI coaching. The common thread? All three architect their solutions around the individual employee as the primary unit of development. They’ve digitized and scaled traditional one-on-one coaching models — making them faster, cheaper, and more accessible. But they haven’t fundamentally reimagined how coaching works in team-based environments.
What Makes Cloverleaf Different
Cloverleaf launched their AI coach in 2018, calling it “Automated Coaching” before the term “AI coaching” existed as a recognized category. Seven years of iteration have produced three distinctive capabilities:
Assessment integration as a competitive moat. Rather than building proprietary assessments, Cloverleaf partners with established providers — Gallup CliftonStrengths, DISC, Enneagram, 16 Types, and others. This creates two advantages:
- Organizations leverage existing assessment investments and language, turning what competitors see as net-new budget into an extension of current spending.
- Coaching guidance grounds itself in validated behavioral science rather than generic AI outputs.
- HR teams consolidate multiple vendor relationships into a single platform.
Proactive coaching, not reactive chatbots. Most AI coaches require users to initiate conversations. Cloverleaf pushes contextual coaching moments automatically into Slack, Microsoft Teams, email, and calendars:
- Pre-briefs before 1:1 meetings based on personality dynamics.
- Message rewrites that adapt communication style to recipient preferences.
- Feedback scripts informed by both giver and receiver profiles.
- Meeting debriefs highlighting collaboration patterns and friction points.
The distinction matters because managers don’t have time to remember to use coaching tools. Cloverleaf meets them in their workflow at precisely the moment coaching adds value.
Team-aware intelligence, not individual isolation. This represents Cloverleaf’s most significant departure from competitors. The platform maps relationships, communication style conflicts, and team dynamics:
- Identifies potential friction before it escalates based on assessment data across team members.
- Provides managers with team dashboards showing strengths, gaps, and collaboration risks.
- Delivers coaching that accounts for group context, not just individual challenges.
- Enables role-playing scenarios informed by actual teammate profiles and interaction patterns.
Organizations using Cloverleaf report a 33% increase in high-quality teamwork and 31% improvement in overall communication, metrics that reflect systemic change rather than individual skill gains.
Who Benefits Most from This Approach
Cloverleaf targets mid-market to enterprise organizations with complex, distributed workforces. Their sweet spot includes:
Professional services firms (consulting, accounting, engineering, architecture) where:
- Teams form and reform around client engagements.
- Communication effectiveness directly impacts billable hours and client satisfaction.
- Remote collaboration creates opportunities for misunderstanding.
- Assessment-driven insights accelerate trust-building in new team configurations.
Consumer products companies managing cross-functional product development teams that:
- Bring together marketing, operations, supply chain, and sales perspectives.
- Navigate competing priorities and communication styles.
- Require coordination across departments with different organizational cultures.
- Benefit from shared language around behavioral preferences.
Government agencies with distributed teams facing:
- Limited traditional coaching budgets.
- Diverse workforce demographics requiring inclusive development approaches.
- Cross-agency collaboration challenges.
- Need for scalable solutions that work across geographic locations.
Technology companies experiencing rapid growth where:
- Engineering teams struggle with feedback culture and manager effectiveness.
- Hybrid work models strain team cohesion.
- Assessment familiarity already exists (many tech companies use CliftonStrengths, DISC, or similar tools).
- Manager enablement at scale determines organizational success.
Organizations already using talent assessments represent the highest-value prospects. If an organization has invested in behavioral assessment infrastructure and built organizational language around those frameworks, Cloverleaf accelerates ROI rather than competing for budget.
Why This Matters Now
Most L&D organizations measure completion rates, knowledge retention, and individual skill development. They miss the crucial question: Can people apply these skills collaboratively? When managers take feedback training individually, they learn frameworks. When they practice feedback within their actual team context, with coaching that accounts for their team members’ communication preferences, they change behavior.
Cloverleaf’s focus on learning effectiveness, not just learning delivery, positions them uniquely. While competitors chase enterprise accounts by matching feature checklists and pricing models, Cloverleaf asks a different question: How do we make development sustainable in the actual environment where work happens?
For organizations evaluating AI coaching solutions, Brandon Hall Group’s Enterprise Institute™ membership provides access to our research on AI adoption, benchmarking against peers, and advisory support for technology selection decisions. Our analyst team regularly briefs members on emerging providers and market trends to inform evaluation processes.
The Road Ahead
As AI coaching moves from early adopters to mainstream buyers, Cloverleaf faces both opportunity and challenge. The opportunity: Organizations are finally educated on AI coaching value and actively running selection processes. The challenge: Increased competition from well-funded players and the ongoing need to differentiate team-focused capabilities from individual coaching solutions.
Three strategic advantages should sustain Cloverleaf’s momentum:
First, their seven-year head start created product sophistication that competitors can’t replicate quickly. Building team-aware AI coaching requires more than adding collaboration features to individual coaching bots; it demands a fundamentally different architecture.
Second, the assessment partnership strategy creates switching costs. Organizations invested in CliftonStrengths or DISC don’t want to abandon that investment. Cloverleaf makes existing tools more valuable rather than replacing them.
Third, the learning effectiveness positioning resonates with a persistent pain point. Every L&D leader struggles to demonstrate impact beyond activity metrics. Coaching that improves team performance, not just individual knowledge, provides clearer ROI stories, the kind of measurable results we highlight through our HCM Excellence Awards® program.
The AI coaching category will continue maturing rapidly. Buyers will become more sophisticated, demanding integration depth, outcome measurement and demonstrated impact. Cloverleaf’s bet on team development as the differentiator appears well-timed. As hybrid work persists and cross-functional collaboration intensifies, the organizations that crack team effectiveness — not just individual capability — will win the talent war.
For L&D and talent leaders evaluating AI coaching solutions, the question isn’t whether to adopt this technology but which approach aligns with how work actually happens in your organization. If your success depends on effective teams rather than brilliant individuals working in isolation, that answer should guide your selection process.
