Leveraging Expertise From
Our 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 instinct to Customer Success. The work covers the full arc post-sale from first handoff to lasting advocacy.
Each win sets up the next. Accounts grow. Product, marketing, and sales draw on customer insights yielding less operational friction and more informed feedback loops.
Clear goals. Repeatable processes. Sustained long-term growth.
Leveraging Expertise Into Results
Chad Olsson, Founder
high-growth saas
E-
commerce
Chad Olsson brings a nearly 20 year track record of growth-minded & operational expertise in leading engagements.
Chad's perspective is shaped by formative experiences across startup models as well having built and led Customer Success groups for 10 years at organizations including DISH Network, Grubhub, and, most recently, with Wix as Head of Global Key Accounts.
With Wingover Advisory, Chad steps in where Customer Success needs to be formed or rebuilt. Drawing on his background, he builds or sharpens customer segmentation so coverage matches what each account warrants based on priority. Chad then optimizes each stage from onboarding to expansion. Working cross-functionally, he ensures customer insights reach every team and inform priorities.
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 & smoker, traveling, and being an avid fan of the Denver Broncos and Colorado Buffaloes.
startups
franchise & wholesale
platforms
30%+
Growth Rate
Partnering With Wingover
Wingover Advisory embeds fractional Customer Success leadership inside the team - not just a report handed over from the outside. The design is a leader in the seat who owns the outcome.
The work centers on building the CS engine to power long-term growth. Existing customers get a clear path from onboarding to adoption to retention to expansion. Customer insight then flows across the organization so every team works from the same picture. Growth inside the customer base rises and friction across the company falls.
The result? Customers who reach value faster, stay longer, and grow long-term.
Roadmap
Developing a customized strategic path with prioritized milestones & deliverables along with clear success metrics to transition insights into action
Implementation
Working alongside your team to implement frameworks, refine systems, and empower leaders as strategy becomes operational reality drives enduring success
Assessment
A concentrated deep dive into customers, data, and the current Customer Success motion to find what works and what holds growth back.
55%+
Faster
Client Onboarding
50%
Revenue
Churn Reduction
97%+
Revenue
Retention Rate
FAQ's
Let's Build Together
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