Kyle Geisler

Between vision and value,
the magic happens.

I help business leaders navigate technology adoption, build organizational alignment, and realize business outcomes with measurable results.

Good enterprise technology decisions require three things most advisors don't have: full grasp of the business priorities, deep technical understanding, clear line of sight to the financial case.
That's where I come in.

business-strategy.sh
$ █

Outcomes Focused. Results Driven.

Technical Fluency Meets Business Acumen

Where Technical Depth Meets Business Impact

Technical Fluency Meets Business Acumen

Most technology advisors specialize in one domain. I work across both—which means I understand not just what's technically possible, but how technical decisions cascade into financial and business consequences. That rare combination lets me translate complexity into clarity for executives at every level.

  • Terminal to Boardroom: I'm equally comfortable in deep technical architecture discussions with your CTO and strategic financial conversations with your CFO. This isn't learned—it's lived across 20+ years of technology and business leadership. When technical and business leaders are speaking the same language, better decisions happen.
  • Technical Complexity Without Technical Bias: I understand infrastructure, cloud, AI, and automation deeply enough to know what's actually possible—and honest enough to acknowledge where technical elegance doesn't equal business value. I help organizations distinguish between "this is technically cool" and "this solves a business problem."
  • Financial Consequences of Technical Decisions: Every technical architecture decision has financial implications. I assess those implications upfront, not as an afterthought. This means business cases are built on realistic technical understanding, and technical strategies are grounded in financial reality.
  • Bridge the Translation Gap: Most organizations have technical teams and business teams that don't speak the same language. That gap creates misalignment, missed opportunities, and expensive mistakes. I bridge that gap by translating between domains—ensuring your organization makes decisions with full clarity.

Financial Modeling & Business Case Justification

ROI Models That Hold Up Under Scrutiny and in Execution

Financial Modeling & Business Case Justification

Building a business case is easy. Building one that CFOs approve and that actually holds up in execution is hard. I specialize in the latter. My financial models start with business priorities, ground assumptions in industry reality, stress-test for risk, and communicate with the rigor that executive teams expect. The result: business cases that get approved and initiatives that deliver on their financial promises.

  • Start with Business Priorities, Not Templates: Most ROI models are built backwards—take a solution, estimate its cost, calculate generic cost savings. I build forwards—start with your business priorities, understand the financial impact of solving them, and model what investment is required. This approach ensures the financial case is actually connected to what matters most to your business.
  • Model Five-Year Impact with Realistic Assumptions: Business case models are only useful if they're realistic. I build in the friction of real implementation: migration complexity, organizational change management, skills ramp-up time, phased adoption. I model multiple scenarios (conservative, realistic, optimistic) so executive teams understand the range of potential outcomes. This prevents the "we predicted savings that never materialized" problem.
  • Connect Technical Decisions to Financial Consequences: When I model infrastructure consolidation, cloud adoption, or AI implementation, I translate technical decisions into financial impact. Moving from dedicated storage to hyperconvergence means specific cost reductions that I can quantify. Adding automation means specific labor reductions that I can model. This connection between technical and financial is what makes the business case credible.
  • Communicate Financial Logic Clearly: Business cases fail not because the math is wrong, but because executives don't understand the logic or trust the assumptions. I present financial models in a way that shows the logic chain: business priority → solution capability → financial impact. I also clearly call out assumptions and where I'm most uncertain. This transparency builds confidence and approval.

Executive Presence with Humble Approach

Earned Authority Through Competence and Genuine Interest

Executive Presence with Humble Approach

I earn influence through competence and genuine interest in your success, not through title or positional authority. This means every engagement is built on demonstrated expertise, transparent thinking, and authentic commitment to your outcomes. I don't pull rank or resort to "trust me, I'm the expert." Instead, I build credibility through clear thinking, substantive insights, and genuine partnership.

  • Deep Research Before Engagement: Before I talk to your team, I've studied your company, your market, your financials, and your leadership. This preparation allows me to engage substantively from the first conversation. It also signals respect for your time and demonstrates that I'm taking the engagement seriously. Your team appreciates advisors who've done their homework.
  • Transparency in Analysis: I show my work. When I make a recommendation, I explain the logic, the assumptions, and where I'm most uncertain. This transparency allows your team to evaluate recommendations critically—not just accept them. When your team understands the reasoning, they're more likely to be committed to implementation and more likely to refine approach as circumstances change.
  • Genuine Curiosity About Your Business: I'm not checking boxes or applying a template. I'm genuinely interested in understanding your business, your challenges, and what matters most to your leadership. This curiosity creates space for your team to think out loud, to raise concerns, and to collaborate on solutions. It also means I catch important nuances that surface-level consulting misses.
  • Commitment to Your Long-Term Success: My interest isn't in a one-time engagement that looks good on a resume. It's in helping your organization develop capability, make better decisions, and achieve outcomes that matter. This long-term perspective influences everything I do—I'm optimizing for your sustained success, not for short-term wins that create dependency.

Track Record at Scale

Proven Ability to Design, Build, and Execute at Enterprise Scale

Track Record at Scale

I haven't just advised on transformation — I've designed and led major initiatives affecting thousands of people and millions of dollars in business impact. This operational experience means I understand not just strategy, but execution: how to build teams, enable large organizations, drive adoption, and sustain impact. I bring that hard-earned operational wisdom to every advisory engagement.

  • Generated $100M+ in Net Revenue Through Program Design: I architected and scaled a sales program that generated $100M+ in net revenue across hundreds of enterprise sellers. This wasn't a one-time success—I took a repeatable sales play, systematized it, and built the incentive structures, training, and management disciplines to scale it to 600+ salespeople. This experience means I understand how to design programs that actually work at scale.
  • Trained and Coached 3,000+ Enterprise Sellers: I've built training frameworks and coaching models used by thousands of sales professionals. I know what works when trying to change behavior across large, distributed organizations. I know where training fails (spoiler: most of the time) and how to design programs that actually drive adoption and performance improvement. This scales the impact of strategy.
  • Led Product and Tooling Teams Through Multiple Releases: I've managed teams that delivered five on-time product releases while driving adoption across a global sales organization. This experience taught me about dependencies, stakeholder management, resource constraints, and the difference between shipping something and actually getting people to use it. These operational lessons transfer directly to transformation initiatives.
  • Advised C-Level Teams on Multimillion-Dollar Decisions: I've engaged directly with hundreds of C-level executives — CFOs, CIOs, business unit heads — helping them make decisions about infrastructure investments, cloud adoption, transformation initiatives worth billions. This executive engagement experience means I understand the pressures executives face, the questions they ask, and what builds confidence in major strategic decisions.

Deep Industry Expertise

Vertical Expertise That Informs Every Decision

Deep Industry Expertise

I've spent significant time in four industries where infrastructure strategy directly impacts competitive advantage: financial services, logistics and operations, enterprise software, and healthcare. This isn't academic knowledge — it's lived experience working with C-level teams navigating industry-specific challenges. That depth means I understand not just your technology needs, but your business model and what drives value in your market.

  • Financial Services: Infrastructure Efficiency Becomes Profit: In banking and finance, every dollar saved in infrastructure flows directly to the bottom line. I understand the regulatory complexity, the infrastructure investment levels, and where optimization creates outsized business impact. When I work with financial services leaders, I'm not just optimizing for cost—I'm optimizing for profit.
  • Logistics and Operations: Technology Amplifying Human Capability: Most value in logistics comes from process efficiency and speed. Technology matters most when it removes friction from human-driven processes. I understand how to identify those opportunities, where technology creates asymmetric advantage, and how to build business cases that resonate with operations leaders focused on throughput and reliability.
  • Enterprise Software: Speed vs. Discipline: Software manufacturers are caught between the need for development velocity and the danger of hastily made technology decisions that create technical debt or vendor lock-in. I've worked with software leaders navigating this tension, helping them make deliberate choices about cloud adoption, infrastructure repatriation, and capability development without sacrificing speed.
  • Healthcare: Compliance, Consolidation, and Growth: Healthcare CIOs face relentless pressure: regulatory compliance, consolidation initiatives, rising operational costs, and need to support growth. I understand these dynamics and how to design infrastructure strategy that addresses all of them simultaneously. This means recommendations that actually work in healthcare's unique operating environment.

Enterprise Sales Strategy & Channel Enablement

From Sales Strategy to Field Adoption to Business Results

Enterprise Sales Strategy & Channel Enablement

Enterprise sales requires alignment across strategy (what are we selling and to whom), tactics (how are we engaging customers), execution (are we following process), and outcomes (are we hitting business targets). Misalignment in any of these areas destroys results. I help organizations align across all four dimensions, then build the management disciplines to maintain alignment.

  • Build Sales Strategies Around Business Priorities: Sales strategy should serve business strategy, not operate independently. I work with organizations to align sales strategies with business priorities: What customer segments are most valuable? What solutions matter most? What outcomes are we trying to achieve? Then I translate this strategy into sales activities and performance metrics.
  • Create Sales Methodologies That Enable Success: Generic sales methodologies don't work. I help organizations develop or adapt methodologies that fit their specific context: their customer types, their solutions, their competitive environment, their sales team capabilities. Then I build training and coaching systems that help salespeople use the methodology consistently.
  • Establish Metrics That Drive Right Behavior: Sales teams do what they're measured on. I help organizations establish metrics that drive the behaviors that create long-term business value: pipeline quality, sales cycle, win rate, deal size, customer success in implementation. These metrics get tracked, reviewed in pipeline meetings, and included in compensation decisions to maintain alignment.
  • Build Manager Coaching Capability: Frontline managers are the key to sustained improvement. I help organizations train managers to coach salespeople on methodology, capability development, and performance improvement. This creates a system of continuous improvement that doesn't depend on corporate enablement or consultants.