In this episode of the OKR Podcast, Deidre sits down with Lou Maiuri, Chairman and Group CEO of AssetMark, to explore how disciplined execution enables speed in a highly competitive, consolidating industry. Lou shares lessons from leading organizations ranging from startups to global banks with 50,000 employees, and explains why he brought OKRs and WorkBoard with him to AssetMark. The conversation explores how leadership cadence, transparency, and WorkBoardAI-powered insights help AssetMark align 1,200 employees around complex, cross-functional growth initiatives—and why finding issues early is critical to winning the race on execution.
The Challenge
- Disconnected, overloaded annual plans obscured priorities:
Individual plans were “filled with too many priorities” (business agenda + personal development + goals), making it easy to “lose the plot” on what mattered most.
- Siloed execution limited cross-functional delivery:
Work ran effectively “north to south” within divisions, but AssetMark struggled to execute initiatives that required teams to work horizontally across functions.
- Late discovery of slippage created expensive interventions:
Without a tighter operating cadence, leaders risked finding out “three, four months” later that work was significantly behind schedule, forcing costly recovery efforts.
- Insufficient visibility into resourcing and feasibility risks:
Major objectives surfaced realities like under-resourced teams, misestimated complexity, and overly aggressive timelines, but these issues were not consistently exposed early enough to adjust.
The WorkBoardAI Solution
- Operational cadence that enables faster course correction:
WorkBoard became embedded into weekly, monthly, and quarterly rhythms—reducing “pay me later” interventions by identifying issues early enough to correct.
- Enterprise-wide transparency and alignment on what matters:
Leaders and employees gained clarity on “major initiatives,” enabling people deeper in the org to articulate priorities and how their work connects to strategy.
- Higher-quality execution through better resourcing conversations:
Reviews shifted from status reporting to actionable problem-solving (e.g., “I need four people, not three”), improving decision-making on capacity and scope.
- Executive leverage via WorkBoardAI insights and data freshness:
Lou used AI agents for weekly summaries and one-on-one prep, plus freshness reporting to keep updates current—driving consistent adoption and reliable visibility.
Conclusion
AssetMark used WorkBoardAI to embed OKRs into the operating rhythm of the business, reviewing progress weekly, monthly, and quarterly at the executive and operating committee levels. Over a year into adoption, Lou reports that 70–80% of strategic objectives are hitting the mark, with the remaining initiatives close enough to recalibrate rather than fail outright. The platform supports alignment across 1,200 employees in multiple U.S. locations, helping teams work horizontally on complex initiatives such as expanding in the RIA channel and bringing private markets to mass-affluent investors. WorkBoardAI enables earlier detection of resourcing gaps, timeline risk, and execution bottlenecks—often within weeks instead of quarters—allowing leadership to course-correct before delays become costly. As a result, AssetMark is executing more initiatives in parallel, reallocating resources more precisely, and building the organizational muscle needed to support a widening 2026 strategic agenda, while maintaining strong service outcomes, including an NPS of 73.
