OLSYS closed multiple high-value enterprise deals by rebuilding GTM and sales enablement across key software verticals.
Founded
2017
Company type
Private company
Industry
Enterprise IT services and software
Company stage
Enterprise
Team size
200+
Engagement
Full-Stack B2B Marketing (CMO)
Collaboration
1 year
Published
Enterprise deals
High-value enterprise deals closed
40%
Increase in MQLs
Results
Multiple high-value enterprise deals in 6 months. MQLs rose 40% across campaigns spanning all 5 verticals: FinTech, MedTech, MSP, AI Engineering, and Legacy Transformation.
A new sub-brand, Dynasphere Technologies, launched for the US automotive vertical. 40+ client case studies were packaged into ICP-facing proof assets.
Overview
OLSYS is a Chicago-based enterprise IT services and software company serving US mid-market enterprises across FinTech, MedTech, MSP, AI Engineering, and Legacy Transformation.
I joined as Head of GTM & Enterprise Marketing in 2025 to architect go-to-market strategy across all 5 verticals and run a full website overhaul: positioning, messaging, and service and industry offerings.
Scope
Architected go-to-market strategy across FinTech, MedTech, MSP, AI Engineering, and Legacy Transformation, each targeting US mid-market enterprises.
Led a full website overhaul covering positioning, messaging, and service and industry offerings.
Built sales enablement assets that closed multiple high-value enterprise deals in 6 months.
Launched a new sub-brand, Dynasphere Technologies, for the US automotive vertical.
Ran go-to-market orchestration for GenOLSYS, a new agentic AI platform.
Packaged 40+ client case studies into ICP-facing proof assets. Manages a design and marketing contractor team of 4 to 5.
"Before this, we pitched every vertical the same way. George gave us the sharp positioning for all our verticals: FinTech, MedTech, AI Solutions, Enterprise Software Dev, and more. We closed multiple high-value enterprise deals in 6 months."
OLSYS Global
IT Enterprise Firm
Impact
A single GTM rebuild now runs across 5 enterprise verticals in parallel, each with its own positioning and proof.
MQLs are up 40%.
Multiple high-value enterprise deals closed within 6 months.
The case study library (40+ client wins) gives every vertical its own ICP-facing proof instead of one generic pitch.
FAQs
How did OLSYS close high-value enterprise deals in 6 months?
By rebuilding go-to-market strategy and sales enablement assets separately for each of 5 enterprise verticals, FinTech, MedTech, MSP, AI Engineering, and Legacy Transformation, so buyers in each vertical saw messaging built for them specifically.
What drove OLSYS's 40% increase in MQLs?
Campaigns run across GTM and content for all 5 verticals, backed by a full website overhaul covering positioning, messaging, and service and industry pages.
What is Dynasphere Technologies?
A new sub-brand launched for OLSYS's US automotive vertical, including its own go-to-market, website, and positioning.
How is OLSYS's case study library used?
40+ client case studies were packaged into ICP-facing proof assets, giving each vertical its own evidences.
Does OLSYS's multi-vertical GTM model apply to other enterprise service companies?
Yes. Running separate positioning and sales enablement per vertical, rather than one message for every buyer, is the mechanism, not something specific to IT services.
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