2022 — Present
Chief Operating Officer
Deepdesk
Leading the operational engine combining human expertise with AI-driven automation. Driving 2x year-over-year revenue growth.
STRATEGIC ADVISORY • AI CONSULTING • ORGANIZATIONAL DESIGN
Navigate Your Next Inflection Point
Through The Second Step, I partner with both high-growth SaaS companies and enterprise organizations to navigate critical inflection points — from early commercial build-out to AI-driven transformation.
SERVICES
What I Do
Scale-Up Strategy
Designing and implementing scalable Sales, Marketing, and Operations functions for start-ups and scale-ups ready for their next growth phase.
AI Advisory
Advising enterprises on AI strategy, use-case definition, and technical adoption paths that deliver measurable results.
Compliance & AI
Helping organizations integrate AI responsibly within complex compliance frameworks — including ISO 27001 and SOC 2.
Leadership & Culture
Supporting leadership teams with mission, vision, culture, and organizational design for sustainable growth.
20+Years Experience
SaaS & EnterpriseDual Market Expertise
AI-FirstStrategy & Deployment
EXPERIENCE
A Career Built on Scaling Impact
2021 — Present
Principal Owner
The Second Step
Partnering with high-growth SaaS companies and enterprises to navigate critical inflection points.
2020 — 2022
VP Marketing
Surfly
End-to-end B2B international enterprise marketing strategy. Scaled from seed to multi-country operations.
ABOUT BRENDAN
Brendan Jackson
Principal — The Second Step
Building, growing, optimizing, and leading start-ups and scale-ups for over two decades. Currently focused on helping enterprise organizations implement results-focused AI solutions within complex compliance environments.
As COO at Deepdesk, I lead the operational engine combining human expertise with AI-driven automation — overseeing Sales, Marketing, Customer Success, Legal, Compliance, HR, and Finance.
I bring together 20+ years of scaling companies with hands-on experience deploying AI in large, regulated environments.
COMPANIES I'VE WORKED WITH
Partners on the Journey
From scale-ups to global enterprises — the teams I've helped grow, transform, and lead.
Deepdesk
Rabobank
bol
Swisscom
Everyone.org
Surfly
FAQ
Common Questions
How do engagements typically start?
Most partnerships begin with a focused discovery conversation and a 30-day diagnostic sprint to define priorities, risks, and measurable outcomes.
Do you work with both start-ups and enterprise teams?
Yes. I support growth-stage SaaS operators and large organizations navigating AI adoption, operating model shifts, and cross-functional execution challenges.
What outcomes should I expect?
Clients typically gain sharper strategic focus, faster cross-functional alignment, and execution plans tied to revenue, adoption, and operational performance metrics.
Ready to Take the Second Step?
Whether you're scaling a start-up, transforming an enterprise, or navigating AI adoption — let's talk about how I can help.
Schedule a Conversation