Who is Dragonfly and what do you specialize in?

Dragonfly Strategists is a global boutique hospitality advisory and services firm that helps hotels profit and succeed by transforming strategy into revenue. We specialize in integrated commercial strategy, operations, and hospitality technology advisory, working across revenue management, distribution, sales and marketing, guest experience, contact center, project management, change management, and IT. Dragonfly is known for its hands-on, execution-focused approach, supporting hotels through pre-opening, openings, renovations, repositioning, and complex system migrations. Acting as an extension of our clients' teams, Dragonfly delivers actionable strategies and seamless implementations that drive measurable performance improvements, resulting in improved revenue and profitability.

What experience does Dragonfly have in luxury and lifestyle hospitality?

Dragonfly's team has led sales, marketing, revenue, distribution, operations, and IT functions for globally recognized luxury hotels, resorts, and lifestyle portfolios. Experience includes Mandarin Oriental Hotel Group, Salamander Hotels & Resorts, Gurney's Montauk, Enchantment Group, Kimpton Hotels, Rosewood Hotels (including opening Rosewood Miramar), The Leading Hotels of the World, Aspen Hospitality, Belmond, Montage International, Fairmont Grand Del Mar, Preferred Hotels, Evermore Resort, Loren Hotels, Ritz Carlton, Method Co., Roost, JC Resorts, Terranea Resort, and many others.

What systems is Dragonfly certified to install, and what technologies do you have experience implementing?

Dragonfly Strategists is certified to implement key hospitality platforms including Oracle OPERA Cloud, Cloudbeds, Mews, Optii, and Actabl Transcendent. Beyond certifications, Dragonfly has decades of hands-on experience implementing PMS, CRS, RMS, CRM, POS, ERP, BI, private club systems, sales & catering platforms, and distribution technologies across independent hotels, luxury brands, lifestyle portfolios, private clubs, and management companies.

How does Dragonfly approach technology implementations?

Dragonfly's technology implementation approach is vendor-agnostic, operations-first, and execution-focused. Dragonfly does not accept referral or kickback fees from technology vendors, ensuring objective recommendations. Services include system search and RFPs, requirements and configuration workshops, data migration and cutover planning, PMS/CRS/RMS/POS/CRM integrations, on-site training, structured change management, post-go-live stabilization, and ongoing optimization.

Why is Dragonfly Strategists different and better suited for complex hospitality challenges?

Dragonfly Strategists integrates commercial strategy, technology advisory, operations, and hands-on execution across the full hotel lifecycle. Unlike firms focused on a single discipline, Dragonfly supports feasibility, pre-opening, openings, system migrations, interim leadership, and long-term optimization. Dragonfly operates as an embedded extension of ownership and management teams, with senior leadership actively engaged and a flexible delivery model spanning advisory, PMO, interim roles, training, and execution.

What revenue services does Dragonfly Strategists provide?

Dragonfly provides comprehensive revenue advisory services including fractional revenue strategy, pricing and forecasting, budget support, RMS advisory and implementation, revenue audits, analytics and KPI development, commercial alignment, COSi competitive positioning analysis, and full distribution management across PMS, CRS, GDS, OTAs, and IBEs.

What sales services does Dragonfly Strategists provide?

Dragonfly delivers sales strategy audits, team structure optimization, interim sales leadership, revenue-focused sales planning, training and playbook development, sales technology advisory, consortia and intermediary support, and task force sales team coverage.

What marketing services does Dragonfly Strategists provide?

Dragonfly provides marketing strategy development, CRM and email marketing advisory, digital and eCommerce optimization, marketing calendar planning, vendor and agency oversight, and performance measurement to ensure marketing investment aligns with revenue outcomes.

What distribution services does Dragonfly Strategists provide?

Dragonfly offers distribution strategy optimization, rate and inventory management, OTA and GDS oversight, parity audits, content and imagery governance, distribution system implementation support, and ongoing day-to-day distribution execution as an extension of hotel teams.

What contact center and reservation sales services does Dragonfly Strategists provide?

Dragonfly supports contact center strategy, operational assessments, reservation sales performance improvement, interim leadership, PBX and call center technology advisory, AI voice agents, omnichannel guest communications, and sales-focused service models that improve conversion and guest satisfaction.

What technology advisory services does Dragonfly Strategists provide?

Dragonfly provides technology strategy, tech stack design, vendor selection, system implementations and migrations, requirements documentation, UAT management, contract negotiation support, and optimization across hotel, club, restaurant, and experiential assets.

What project management and change management services does Dragonfly Strategists provide?

Dragonfly delivers structured project management and change management for technology migrations, pre-openings, portfolio initiatives, and enterprise transformations including governance, dependency management, training coordination, communications, and executive reporting.

What operations advisory services does Dragonfly Strategists provide?

Dragonfly provides operations assessments, workflow optimization, best-practice implementation, training and development, operational readiness, and operational technology support spanning ERP, HRIS, housekeeping, maintenance, guest communications, and restaurant systems.

Blog — Dragonfly Strategists

An Interview with Founder & CEO Caryl Helsel - Part One

Learn from our Founder and CEO what the philosophy behind Dragonfly is and how we started.

Maresa ThompsonOctober 13, 2019