Keegan Longueira

Responsible for driving new business growth in the UKI region across mid-market and scale-up accounts. Known for top-tier performance, deep product knowledge, and technical sales leadership across complex, multi-stakeholder deals.

Key Achievements:

• Delivered a record-breaking 298% quota attainment in May 2025—the highest-performing month in the region to date.
• Closed the most complex deal in the UKI market to date: a £270,000 multi-hub contract with a high-growth technology company, requiring intensive alignment across legal, product, and technical teams.
• Recognized as the #1 performer across the UKI team in March 2025, consistently ranked in the top 5% of reps.
• Acted as a technical orchestrator on complex deals, working cross-functionally with sales engineers, solution architects, legal, and implementation teams to build trust and clarity across long sales cycles.
• Multi-threaded across C-suite and mid-level champions, navigating complex buying groups with multiple stakeholders across operations, marketing, IT, and finance.
• Led and contributed to AI-first positioning and GTM enablement by building internal resources and narratives that helped product marketing, BDRs, and regional sales leaders sell new AI-powered HubSpot features effectively.
• Frequently tapped to coach peers on large-deal strategy, objection handling, and deal design—especially for technical product rollouts and platform consolidation scenarios.

Skills & Tools:

• Complex SaaS sales | Sales engineering collaboration | AI & automation in GTM
• HubSpot CRM (enterprise suite) | Technical stakeholder management | RFP & procurement alignment
• Pipeline forecasting | Solution-based selling | Strategic GTM input

Brought in as a fractional consultant to scale and systematize BoxMate’s sales and integration infrastructure in preparation for acquisition - Successful Exit in July 2025 (Acquired by DaySmart USA)

• Architected and implemented a modular GTM strategy aligned with engineering sprints and product-market fit, supporting pipeline growth during the lead-up to BoxMate’s successful exit.
• Led a full CRM transformation, including advanced configuration of HubSpot custom objects, API-driven workflows, lifecycle stages, and sales-to-CS handoff logic.
• Collaborated with BoxMate’s engineering team to map, scope, and plan custom API integrations between their platform and external systems (payments, push messaging, third-party apps), ensuring scalable data flow and consistent event capture.
• Defined technical requirements for webhooks, authentication flows, and CRM<>platform syncs, enabling tighter feedback loops between sales, support, and product.
• Co-led stakeholder workshops to align backend data structures with frontend pipeline stages and GTM activities—translating business processes into automated, configurable systems.
• Delivered productised outbound sequences and forecasting dashboards that reduced friction and increased clarity across the sales funnel.

Enterprise sales lead for Daysmart’s expansion into the fitness sector, focusing on complex, multi-location gym software deployments worldwide. As part of the founding GTM strategy team, I helped design the sales motion from the ground up—combining enterprise SaaS strategy with deep technical collaboration.

• Spearheaded high-value deals with multi-site fitness chains, aligning Daysmart’s platform with global operational needs including scheduling, CRM, billing, and reporting.
• Led technical discovery and sales engineering efforts, working with CTOs and IT stakeholders to scope custom API integrations, including secure access control systems, CRM syncs, membership platforms, and third-party fitness ecosystems.
• Drove RFP responses and multi-stakeholder procurement cycles, often involving C-suite, operations, finance, and technology teams across EMEA and North America.
• Negotiated and closed multi-year enterprise contracts, navigating complex buying groups and compliance requirements while maintaining strong commercial alignment.
• Partnered cross-functionally with product, engineering, and solutions architects to translate customer requirements into scalable platform configurations and integration roadmaps.
• Helped define the core enterprise GTM playbook, including sales process, value positioning, pilot frameworks, and objection handling for high-stakes global clients.

Founded and led a portfolio of ventures across endurance expeditions, public speaking, and fitness operations. Delivered measurable business impact while navigating complex stakeholder environments and managing technical and operational components end-to-end.

Key Highlights:

• Raised over €1 million for Mercy Ships and Operation Smile through a record-setting cycling expedition from Cairo to Cape Town, which resulted in a Guinness World Record and international media coverage.
• Secured high-value sponsorship and branding deals, including six-figure partnerships with global companies, by leading structured proposals, aligning stakeholder incentives, and negotiating long-term commitments involving marketing, CSR, and brand alignment teams.
• Collaborated with multiple stakeholder groups—corporate sponsors, PR teams, logistics suppliers, medical charities, and media broadcasters—to deliver large-scale, multi-country campaigns under tight deadlines and public scrutiny.
• Built a personal media platform including authoring three published books, hosting national radio segments, and featuring on television to promote human resilience, storytelling, and mindset—leveraging these platforms to drive inbound speaking and consulting engagements.
• Delivered keynote talks at global enterprises including Glencore and Cipla, tying personal expedition lessons to business performance themes such as grit, growth mindset, and decision-making under pressure.
• Acquired and scaled a fitness business across two physical locations, growing membership to over 300 and tripling recurring revenue through digital optimization, CRM implementation, operational redesign, and staff development.