Offering 05
Executive Advisory
and Fractional Partnership
C-suite partnership for technology leaders navigating the decisions that don't wait for the next quarterly planning cycle.
¹ Ratio of documented client value to engagement fee across RLK engagements. Past results are not indicative of future outcomes. Terms.
² CEB/Gartner research on strategic advisory impact for technology leaders. Compounding returns accrue across multi-year engagement duration.
Who This Is For
The hardest decisions don't fit neatly into a project scope.
Most technology leaders inside mid-market organizations carry the weight of a Fortune 50 CTO (board accountability, large-scale investment decisions, organizational transformation) without the supporting infrastructure those roles typically come with.
This engagement is for leaders who need a trusted thought partner with enterprise-grade strategic depth available throughout an inflection, not just for a discrete six-week sprint.
- CIO / CTO in a New RoleFirst 90–180 days. Stabilizing quickly, building board credibility, and making the early decisions that define the tenure.
- Technology Leader under ScrutinyNavigating a difficult budget cycle, a failed implementation, or a board that has lost confidence in the function.
- Leader Preparing for a TransactionM&A, fundraising, or sale, where the technology function needs a clear story and the leader needs to hold up under diligence.
- Leader Modernizing DeliveryFacing pressure to move from legacy systems or operating models to something the business can actually use, without blowing up what's working.
What This Covers
Regular biweekly working sessions focused on your highest-priority strategic decisions. Prepared, structured, and fast-moving, not status meetings.
Available when the board question lands Thursday or the vendor negotiation accelerates unexpectedly. The decisions that matter rarely respect the calendar.
Building and pressure-testing the narrative that earns capital, credibility, and alignment from boards, sponsors, and investors.
Diligence readiness, technology narrative construction, and executive coaching through acquisition or transaction close.
Facilitated alignment across your direct team, cross-functional peers, and senior stakeholders when priorities conflict or momentum stalls.
What the Relationship Looks Like
Not a retainer. A working partnership.
Weeks 1–2. I develop a complete picture of your organization, your stakeholders, your priorities, and the specific inflection you're navigating. This is not a survey: it's structured conversations designed to get me operational as quickly as possible.
Typically biweekly. A structured working session focused on the highest-priority decisions and strategic issues you're navigating. I come prepared; we move fast. These are not status meetings.
The decisions that matter most rarely respect the calendar. On-call access means I'm available when a board question comes in on a Thursday, a vendor negotiation accelerates unexpectedly, or a leadership situation escalates.
Board presentations, strategic plans, investor narratives, organizational designs: when the inflection requires a document, I build it or build it with you. This isn't advisory at a distance.
Every engagement ends with a set of reusable frameworks, playbooks, or decision structures the organization keeps. You shouldn't need me for the same problem twice.
What You Bring
Inputs
- Clarity on the inflection: what are you navigating and what does success look like at 6 months and 12 months
- Access to the board materials, strategic plans, and organizational context required to get me fully operational
- Willingness to have direct, unfiltered conversations about what's working and what isn't
- Commitment to a minimum engagement period (typically 90 days) sufficient to navigate the inflection meaningfully
What You Get
Outputs
Why RLK vs. Alternatives
What you don't get from a coaching retainer or a fractional exec placement.
Business Case
What ongoing strategic partnership produces at inflection points.
CTO entering a new role in a PE-backed company. Prior CTO had left under difficult circumstances. Worked through a 90-day stabilization plan, rebuilt the board narrative around technology investment, and presented a credible 12-month roadmap. Board confidence scores moved from low to high in a single cycle.
CIO at a healthcare services company preparing for acquisition diligence. Technology function had no coherent narrative, aging infrastructure story, and cost structure that looked bad without context. Built the diligence package, prepared the CIO for buyer Q&A, and navigated the close.
VP Technology under scrutiny after a failed ERP implementation. Board was considering cutting the technology budget significantly. Built a forensic analysis of what actually went wrong, a remediation plan with clear milestones, and a restructured investment narrative. Budget was defended in full.
Important Note
Every advisory engagement is shaped by the specific inflection the leader is navigating. The timelines, outputs, and results described here are illustrative. Your engagement will be scoped specifically to your situation. We define success together before the work begins, and I'll tell you directly if this model isn't the right fit.
Start the Conversation
Navigating something that doesn't fit a six-week sprint?
Tell me what you're facing. Most advisory relationships start with a single direct conversation.
Connect with Ryan →