Explore Leadership Advisory Services with Stephen Taylor
Every engagement is personal, specific, and grounded in 25 years of hands-on product leadership and AI deployment in the most demanding regulated markets in the world. A small number of clients are taken on at any one time — deliberately.
Executive Coaching for Product Leaders in Fintech and Regulated SaaS
WHO IT IS FOR: VPs and Heads of Product (or fast-track Directors) in high-stakes regulated B2B sectors. Leaders navigating the leap from execution to enterprise-level strategic influence.
WHAT WE WORK ON: Bridging the gap between scaling product and navigating complex governance, roadmap defensibility, and executive communication. Moving from manager to C-suite leader.
HOW IT WORKS: Long-term one-to-one engagement focused on leadership precision and career acceleration in complex software environments.
Product Strategy and GTM Advisory for Regulated SaaS Companies
WHO IT IS FOR: Series B–D companies and enterprise SaaS platforms in highly regulated sectors (Banking, GovTech, FinCrime) needing C-suite level product advisory.
WHAT WE WORK ON: Embedded advisory covering roadmap precision, SDLC discipline, cross-functional sales alignment, and M&A integration strategy.
HOW IT WORKS: An embedded engagement providing deep strategic capacity without the overhead of a permanent hire.
AI Transformation and Governance Advisory for Regulated Companies
WHO IT IS FOR: Regulated institutions (Tier 1 banks, law enforcement, FinCrime) currently building or deploying production-grade AI systems.
WHAT WE WORK ON: AI product strategy, ethical frameworks, production governance, and operationalizing large-scale AI within strict regulatory shells.
HOW IT WORKS: Specialist advisory founded on hands-on experience deploying AI in the world's most sensitive and demanding security environments.
Common Questions
What is the difference between executive coaching and advisory?
Coaching is focused on you — your development as a leader, your decisions, your career path. Advisory is focused on your company — the product, the team, the strategy. Some clients use both. The right structure is discussed during an initial discovery call at no cost.
Do you work with early-stage startups?
Series B and beyond is the primary focus. Earlier stage companies tend to have founder-specific challenges rather than product leadership challenges. If the fit is not right, you will be told directly and pointed to someone who is better suited.
Can you help us build an AI strategy for a regulated financial services company?
Yes — this is one of the three core service areas. The experience behind this advisory includes production AI deployed for FBI and MI5 investigators, AI analytics layers built for Tier 1 banks, and direct engagement with US Treasury FinCEN on responsible AI policy. The advice is grounded in real deployment, not theory.
Can you help us hire our first CPO or VP of Product?
Role definition, org assessment, and candidate evaluation criteria are all part of advisory engagements. Executive search is not conducted directly, but introductions to specialist fintech and regtech recruiters are available where relevant.
How quickly can an engagement start?
Typically two to three weeks from a signed agreement. A small waitlist is maintained. Availability is confirmed transparently during the first call.