The Wingover Approach
In aviation, a "wingover" is a steep climb followed by a sharp bank in the opposite direction - a maneuver pilots use to bypass trouble and find a clear route forward.
Wingover Advisory brings that same instinct to fractional revenue leadership in building the flywheel between customer success, revenue operations, and marketing. When the three elements reinforce each other, growth compounds. If one slips, the others feel it.
When your organization faces challenges and requires a shift in momentum, Wingover Advisory provides the clarity to pivot and turn complex challenges into precise, actionable strategies.
Partnering With Wingover
Wingover Advisory's model is built on senior expertise with proven results across a wide portfolio of business models and industries.
The result? A data-first process that uncovers & devises strategies to address where revenue is leaking or is underdeveloped and where operational friction is quietly undercutting growth.
30%+
Growth Rate
70%
Faster Client Onboarding
Assessment
A concentrated deep dive into your focus areas including revenue, operational, and marketing health to size up what's working & areas of opportunity
Roadmap
Developing a customized strategic path with prioritized milestones & deliverables along with clear success metrics to transition insights into action
Implementation
It's not just presenting broad recommendations. Working alongside your team to implement frameworks, refine systems, and empower leaders as strategy becomes operational reality is what propels lasting success
Strategic Pillars
Customer Success
Architecting sustainable revenue impact through:
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Shaping business review & customer touchpoint mapping to ensure long-term objective alignment
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Refining new customer onboarding & intake processes to shorten time to value
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Proactive customer health monitoring to identify and address risk factors + growth opportunities
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Utilizing data insights to increase product adoption levels
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Strengthening sales to onboarding & CSM handoff processes
Revenue Operations
Identifying & eliminating friction hindering progress by:
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Transforming complex data sets into custom dashboards & actionable insights
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Implementing AI-backed initiatives to reclaim time from repetitive tasks
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Optimizing CRM: Cleanup, reporting enhancements, etc.
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Analyzing software ROI to ensure tools serve specific goals
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Building forecasting models for predictable growth
Growth Marketing
Connecting spend & messaging to revenue via:
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Designing customer segmentation & executing related marketing plans
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Website analytics analysis: Sales/traffic/conversion trends & tailored recommendations
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Defining key metric baselines, success measures, and reporting to inform budget allocation & ROI
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Constructing lifecycle campaigns to boost customer value
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Evaluating channel performance tied to revenue, not just traffic
Experience Behind Fractional Revenue Leadership
Chad Olsson, Founder
E-
commerce
Chad Olsson brings a nearly 20 year track record of growth-minded & operational expertise to every engagement.
Chad's perspective is shaped by formative experiences across roles in small business and startup models while also having led customer success groups for 10 years across organizations including DISH Network, Grubhub, and Wix. Chad specializes in high-impact revenue strategies, digital optimization, operational design, and leadership & team development.
With Wingover Advisory, Chad focuses on revenue growth & operational refinement by ensuring fundamentals are sound enough to support sustainable growth. He balances operational & organizational health with scaling efforts when designing client solutions.
Chad earned an MBA in International Business from the University of Colorado-Denver and a Bachelor's Degree in Marketing from the University of Colorado-Boulder.
Based in Denver with his wife and two children- Chad is a Colorado native who enjoys coaching and cheering for his kids' teams, manning the grill and smoker, traveling, and being an avid fan of the Denver Broncos and Colorado Buffaloes.
saaS/
Startups
franchise & wholesale
Consumer
Services
Let's Build Together
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