Dale Shephard
Founder & CRO, TrinityHawkDale Shephard — Founder & CRO, TrinityHawk
Dale has spent his career inside complex B2B sales, from enterprise software to the Workday services ecosystem, where as a Client Director he managed a portfolio of UKI customers and led the first post-acquisition sales of Workday Strategic Sourcing (formerly Scout). He has since built commercial functions from zero — including a Workday integration partner that generated £1.5m in its first 12 months with no prior sales capability.
Today he runs TrinityHawk as the embedded commercial engine for high-growth businesses, and is a regular conference speaker on founder-led sales (most recently at Tonik Startup Day).
Writing
Sending isn't selling
Gartner reckon AI agents will outnumber sellers ten to one by 2028, and fewer than 40% of sellers will say it helped. Meanwhile professional services is barely getting cited in AI answers at all. Both of those problems have the same root.
Read article24 August 2026Leaner Or Just Smaller
The go to market data everyone is quoting says teams are shrinking. It does not say what most founders think it says.
Read article17 August 2026The Proof-of-Value Gate: Why B2B SaaS Demos Stopped Closing Deals
HubSpot added 7,000 net new customers against a target of 9,000 to 10,000. Here is what proof-of-value buying means for your pilots, your champion and your board-approved deals.
Read article10 August 2026The Q3 Velocity Squeeze: Why Enterprise Deals Are Stalling
Deal cycles have stretched by 32%. Here is the 2026 blueprint to eliminate procurement friction and accelerate closing velocity.
Read article3 August 2026De-Risking the CRO Search: Why PE Boards Mandate Fractional Leaders First
60% of VP of Sales hires fail within 18 months. Here is how PE boards use fractional operators to de-risk executive hiring.
Read article27 July 2026Beyond SEO: Why B2B SaaS Scale-Ups Must Optimise for AI Search Engines (GEO)
94% of B2B enterprise buyers research vendors anonymously on AI engines before booking a demo. Here is how to structure your GTM for the Generative Engine Optimisation era.
Read article20 July 2026The Death of the Linear Funnel: Why Modern B2B SaaS Demands Account-Centric Orchestration
Enterprise procurement has moved past sequential leads. Here is the 2026 RevOps blueprint for multi-stakeholder orchestration.
Read article13 July 2026The Custobot Era: Why Modern Sales Discovery Demands an Analytical Architect
Enterprise buyers are AI-informed before your reps ever speak to them. Here is how to evolve your sales discovery playbooks for the Custobot era of algorithmic procurement.
Read article6 July 2026The Attribution Illusion: Why AI Search is Blinding Your B2B SaaS CRM Tracking
Your CRM attribution software is lying to you about your pipeline source.
Read article29 June 2026The Valuation Vulnerability: You Can't Hide a Messy CRM from a Private Equity Data Room Audit
Discover why a chaotic CRM can derail your tech exit, how private equity due diligence audits your go-to-market systems architecture, and the frameworks founders need to maximise valuation.
Read article23 June 2026Fractional vs Full-Time Sales Director: The Business Case
For most growing businesses, a fractional sales director delivers the same senior leadership as a full-time hire: strategy, structure, coaching and accountability, at a fraction of the cost and with far less risk.
Read article22 June 2026Beyond the Pipeline Illusion: Why Modern Investors are Auditing Your "Revenue Quality"
If you are a B2B SaaS founder mapping out a path toward an upcoming series investment, growth equity round, or a strategic exit, your financial metrics only tell half the story.
Read article15 June 2026The AI SDR Deliverability Collapse: Why Your Startup Needs a Revenue Architect, Not Another Tool
47% of AI SDR deployments are collapsing within 90 days due to domain destruction. Discover why the 'Toolbox Overload' is failing B2B SaaS and how to build a sustainable, hybrid GTM architecture.
Read article8 June 2026The Over-Informed Buyer Paradox: Why More Data is Stalling Mid-2026 B2B SaaS Sales
Why are B2B SaaS sales stalling when buyers have more information than ever? Discover how the Over-Informed Buyer Paradox is changing mid-2026 GTM strategy and why fractional sales leadership is the antidote.
Read article24 May 2026The 5 legal mistakes quietly destroying your agency's margins
You don't need a law degree. You need to stop making these five completely avoidable errors.
Read article20 May 2026Why Founder-Led Sales Always Stalls (and What to Do About It)
Every founder can sell. The problem is they can only sell when they're in the room. Here's why that creates a ceiling — and how to break through it.
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