Sessions · Advisor session
How to Time and Structure a Seed Raise That Closes
Thursday, October 1, 2026 · 2–3 PM PDT
This session has ended.
About this session
Most founders start raising before their story and metrics can carry the round, then burn months learning the investor bar the hard way.
For one hour, we'll dig into how to time and structure a seed raise with Randy Wootton, Partner and Coach at CEO Coaching International. He led the merger of SaaSOptics and Chargify into Maxio as CEO, serving more than 2,200 B2B SaaS customers.
This is about timing, sizing, and structuring an early raise and choosing the right vehicle. It is not a pitch deck critique or a Series B growth-equity discussion.
What you'll work through:
Reading whether your traction clears today's seed bar, or whether to wait
Sizing a round and runway so the raise buys real milestones
Choosing between angels, a syndicate, and institutional seed money
Running a first-time process solo without losing momentum
If you have a seed or angel raise in front of you, bring it.
Hosting this session
Randy Wootton
Chief Client Officer, CEOCoaching
I get tremendous energy from helping leaders and teams unlock their potential and overcome immense challenges.
I am now doing this as a Partner/ Coach with CEO Coaching International—one of the top 1:1 coaching outfits in the industry.
Earlier in my career, I helped Microsoft and Salesforce achieve triple-digit revenue growth rates by focusing on our customers' thorniest problems. I brought this same approach as CEO to RocketFuel & Percolate, where I was brought on to redefine the strategy and drive executional rigor for each company. By doing so, we executed two successful exits. After selling Percolate to Seismic (the leader in Sales Enablement), I stayed on as Chief Strategy Officer for 2 years. In this role, I oversaw two acquisitions and one strategic investment (total value $300M+).
In 2022, I was tapped by Battery Ventures to take over the integration of SaaSOptics and Chargify, which they had purchased in 2021. My team and I launched a new brand, "Maxio,” built new capabilities, and executed an acquisition to support Maxio's vision to help start-ups accelerate their growth. With more than 2200+ customers, Maxio is the industry-leading billing and financial operations platform for B2B SaaS companies.
I left Maxio in April 2025 and started my own CEO advisory service firm, CEOx, to work with AI-first and Agentic AI companies to build scalable GTM engines and org infrastructure.
I joined CEO Coaching International in Nov 2025 to broaden and deepen the impact I can have.
Over the years, I have served on several boards, including Guidant (a tech-enabled service company helping entrepreneurs finance their dreams) and currently at Opal (a content marketing platform).
Early in my career, I spent 12 years in the Navy, and I’m deeply passionate about veterans affairs, which is why I co-founded Vetforce.org at Salesforce.com. Finally, I care a lot about children’s education and have served on the YMCA (Embarcadero Branch) and the Boyer’s Children’s Clinic's Board over the years.
When I’m not at work, I love being outdoors — biking (all types), hiking, and skiing with family and friends in Sun Valley, Idaho.
Next step
Have a question behind the session?
Share what you’re working through. If your company qualifies, we’ll reply personally within 24 hours.
For companies that have raised at least $1M from venture firms.