How I Helped Wheresight Build a LinkedIn-Led GTM Foundation for the North American DMO Market

Quick Snapshot

Across an eight-week pilot and a three-month retainer, I helped Wheresight move from less structured LinkedIn activity toward a coordinated GTM foundation for the North American DMO market.

• Developed clearer positioning around digital maturity, operator readiness, and bookability
• Improved the LinkedIn profiles and content direction of two Wheresight spokespeople
• Built campaign assets around the DMA Scorecard, LinkedIn Live and AI Report
• Connected content with commenting, report promotion, direct messages and structured outreach
• Generated measurable visibility, report interest, relevant conversations, meetings and pipeline signals

The Client and the Challenge

Wheresight helps destination organisations measure and improve the digital maturity, bookability and digital readiness of tourism operators.

The company needed a clearer way to communicate a complex offer to DMO leaders and destination teams. Its LinkedIn activity also needed stronger connections between spokesperson profiles, content, engagement, conversion assets, targeted outreach and commercial follow-up.

The main challenge was not a lack of LinkedIn posts.

Wheresight needed a system that made its value easier to understand and supported relevant business conversations in the USA and Canada.

Goals of the Collaboration

• Clarify Wheresight’s market positioning and digital maturity narrative
• Strengthen spokesperson profiles and authority
• Turn specialist knowledge into consistent and useful
• LinkedIn content
  Build conversion assets around the DMA Scorecard and AI Report
• Connect content with relevant engagement and targeted outreach
• Create a measurable base for conversations, meetings and commercial follow-up

What I Did

I developed and supported a LinkedIn-led GTM system across positioning, profile optimisation, content, engagement, authority assets, conversion paths and outreach.

• Market positioning and message development
  LinkedIn profile optimisation for Karl Llewellyn and Darragh O’Rourke
• Profile banners, headlines, About sections and Featured-section direction
• Content strategies, content matrices, post development and quality review
• DMA Scorecard positioning, landing-page copy and email follow-up
  LinkedIn Live planning, hosting, promotion and replay distribution
  LinkedIn articles, newsletters, Beehiiv content and video repurposing
• AI Report campaign strategy, landing-page direction and follow-up assets
• Commenting and engagement workflows
  Targeting, outreach messaging, Activate5 support and response review
• Weekly guidance, implementation support and reporting

Phase 1: Eight-Week LinkedIn Pilot

The first phase ran from January to March 2026 with Karl Llewellyn as the main spokesperson.

The pilot established Wheresight’s initial LinkedIn GTM foundation. We refined the company’s positioning, strengthened Karl’s presentation as a spokesperson, and built a coordinated campaign around the Digital Maturity Accelerator, DMA Scorecard, and a LinkedIn Live for DMO leaders.

The LinkedIn Live, Why DMOs Need a Digital Maturity Baseline Before Their Next Budget Cycle, was supported by promotional posts, articles, newsletters, reminders, a replay, native video clips, and distribution across LinkedIn, Beehiiv, YouTube, and TikTok.

• 171 organic registrations
• 165 total viewers
• 265 video views
• 8.9% engagement rate
• 45 social engagements
• 13 reposts

The campaign also generated 2,691 gross pre-event LinkedIn impressions and 3,020 gross post-event LinkedIn impressions. These were distribution totals, not unique-person figures.

Phase 2: Three-Month LinkedIn Retainer

The second phase ran from 17 March to 16 June 2026. It extended the system across Darragh O’Rourke and Karl Llewellyn.

Month 1 focused on Darragh’s profile and the AI Report foundation. The work produced a revised profile, content strategy, monthly matrix, landing-page direction, weekly posts, and an engagement workflow.

• 2,239 content impressions
• 25.4% follower growth compared with the prior 60 days
• 1,753 profile appearances
• 52 comments during the tracked week

Months 2 and 3 shifted the main activation back to Karl. His content focused on DMO enablement, operator readiness, AI maturity, bookability, and practical destination activity.

• 127 new connections during Month 2
• 3,628 post impressions across 11 visible posts
• 17 DMO and tourism conversations
• 5 warm or active replies
  7 to 8 active or warm pipeline signals
• 4 meetings moved to Karl
• 44 AI Report downloads
• 375 structured comment and reply items
• 11,060 visible comment impressions

During Karl’s reported 60-day period, his content generated 10,930 impressions, reached 4,224 members, and produced 342 social engagements. His strongest posts came from real destination activity, operator stories, industry events, bookability issues, and field observations.

Structured Outreach

The final month connected Karl’s content and engagement with an initial Activate5 outreach cycle.

• 103 targeted contacts
• Three-message sequence
• 4 direct replies
• 13 new connections
• 13 inbound response signals
• 19 relationship or discovery entries

Sales Navigator credit limits and sequencing interruptions affected implementation. The outreach results should be treated as an initial benchmark and learning cycle, not a final judgement on Wheresight’s market or offer.

Selected Results

• 171 organic LinkedIn Live registrations
• 44 AI Report downloads
• 127 new Karl connections during Month 2
• 10,930 Karl content impressions during the reported 60-day period
• 11,060 visible comment impressions
• 17 DMO and tourism conversations
• 7 to 8 active or warm pipeline signals
• 4 meetings moved to Wheresight’s commercial lead

These results show positioning, visibility, audience development, report interest, relevant conversations, meetings, and early pipeline activity. They do not represent closed sales.

What Wheresight Said

‘Working with Ivan helped us bring much more structure and consistency to how we use LinkedIn. He sharpened our messaging, improved how we present ourselves, and helped us use the platform in a more focused way. We saw better-fit connection activity, more accepted requests from ICPs, and more responses to direct messages. The process created enough value for us to continue and expand it across the wider team.’

Karl Llewellyn, International Commercial Director, Wheresight

LinkedIn Recommendation

‘Pleasure working with Ivan this year (2026). Our LinkedIn strategy needed fresh eyes and ideas. Ivan did a root-and-branch review and then worked with us to help us apply new practices to increase our audience and engagement. No hesitation in recommending Ivan.’

Karl Llewellyn, Wheresight, August 2026

Video Testimonial

Karl Llewellyn Testimonial: From Pilot to Partnership with Wheresight

https://www.youtube.com/watch?v=rUJn5S_pGms 

What Worked Best

• Clearer spokesperson positioning and profile presentation
• Commenting on relevant DMO, destination and tourism posts
• Authority assets built around practical market problems
• Real destination activity, operator stories and field observations
• Coordinated content, engagement, report promotion and outreach

What We Learned

• Content performs better when it starts with the spokesperson’s real work, visits, photographs, events and observations
• Commenting creates relationship and discovery signals that publishing alone often misses
• Targeting should focus on the person who owns the budget or business problem
• Content, engagement, outreach and follow-up need shared timing and messaging
• Attribution should be planned before launch through source tracking, meeting status, and clear follow-up ownership

Commercial Attribution

The engagement generated stronger positioning, visibility, audience development, report interest, conversations, meetings, and pipeline signals.

Wheresight remained responsible for sales qualification, calls, proposals, negotiation, and final conversion. No closed-client result, revenue result or return on investment is attributed to this engagement without direct client confirmation.

What Happens Next

The collaboration left Wheresight with clearer positioning, stronger spokesperson profiles, reusable campaign assets, a larger relevant audience, a structured engagement workflow, and a more actionable commercial follow-up base.

If your Travel Tech company sells into complex tourism markets and needs LinkedIn to support positioning, authority, conversations, and pipeline development, let’s talk.

Book a call:
https://ai-tourism-innovator.com/book-a-call/