By Dustin Stone, HTN staff writer - 10.6.2025
Plusgrade has acquired Oaky, bringing together two companies that both focus on monetizing guest intent through targeted offers. Plusgrade is best known for ancillary revenue programs in airline and other travel segments, while Oaky is a hotel upselling platform that has been recognized by industry awards for several years. The companies say they will build a single upsell experience that combines pre-arrival offers, room and amenity upgrades, and on-property add-ons. Financial terms were not disclosed. Stifel advised Oaky’s shareholders, a PeakSpan Capital portfolio company, and legal counsel on the transaction included Osborne Clarke for Oaky and Davies Ward Phillips & Vineberg LLP and Stibbe N.V. for Plusgrade. As part of the deal, Oaky co-founder Erik Tengen becomes President, Hospitality Upsell at Plusgrade.
For hoteliers, the strategic idea is straightforward. Most properties already capture some incremental revenue through early check-in, late check-out, room moves and add-ons such as parking, breakfast or spa. The challenge is scale, timing and relevance. Oaky’s value proposition has centered on automating the creation and delivery of these offers with a hotel-friendly workflow. Plusgrade brings a track record of running ancillary programs at high volume across airlines, rail, cruise and hospitality, along with a network of enterprise relationships. If the integration lands as promised, hotels could see a broader catalog of offers, a larger distribution footprint and more mature experimentation and reporting.
The immediate questions are product ones. Customers will want clarity on the migration path, feature parity and pricing. Many hotels have invested time in offer templates, translations, targeting rules and reporting inside Oaky. They will expect those assets to carry over without disruption. The same applies to service levels and data handling. Upsell tools touch reservation, profile and payment data, so continuity on data protection, consent management and PCI requirements will be closely watched. A realistic roadmap that explains when systems converge, how existing contracts will be honored and what changes, if any, occur in support models will do more to build confidence than broad statements about a unified experience.
The competitive context is active. Oracle’s Nor1 remains a reference point for room-upgrade merchandising integrated with OPERA. On the independent side, ROOMDEX built a following with automated pre-arrival upgrades and add-ons, and UpsellGuru has carved out a niche with bid-based upgrades. Duve and Canary Technologies approach upsell as part of a wider guest journey toolset that includes messaging, digital check-in and payments. CRM and marketing platforms like Revinate and Cendyn enable targeted pre-arrival campaigns that can function as de-facto upsell programs for some brands. Revenue management providers are also pushing deeper into attribute-level pricing and packaging, which blurs the line between classic RMS optimization and merchandising logic. In practical terms, buyers have no shortage of options, and the differentiators tend to be integration breadth, automation quality, experimentation tools, user experience for staff, and measurable revenue lift after fees.
This combination gives Plusgrade a clearer hospitality beachhead and signals continued consolidation in upsell and merchandising. Plusgrade’s history in airline ancillary could matter in two ways for hotels. First, it brings playbooks for running always-on experiments at scale, for example controlled tests of offer sequencing, price points and channel mix. Second, it brings experience connecting upsell mechanics to loyalty benefits and co-branded financial services, an area hotels are revisiting as they try to raise capture on direct and member channels. Whether those advantages translate depends on how quickly the company can harmonize data models across systems and deliver usable analytics to hotel teams without adding operational friction.
Integration coverage will be a deciding factor. Successful upsell programs require dependable connections to the PMS for room inventory and folio posting, to the CRS and booking engine for pre-arrival injection, to payments for secure collection, and increasingly to the CRM or CDP for segmentation. Buyers will look for published, maintained integrations with major platforms such as Oracle OPERA, Infor HMS, Agilysys, Mews, Cloudbeds and others, as well as connectors to brand-standard payment gateways and identity systems. They will also look for guardrails that prevent guest fatigue, such as frequency caps, language control and brand governance, along with clear revenue attribution so commercial teams can distinguish true incremental lift from revenue that would have occurred anyway.
The leadership alignment is notable. Retaining Oaky’s product voice through a named operating role suggests Plusgrade intends to preserve, then extend, what Oaky customers already value. The risk in any merger of this kind is dilution of focus while teams rebuild a combined stack. The upside is a broader data set, more engineering resources and a larger partner ecosystem. If Plusgrade can keep implementation simple, protect existing gains for Oaky customers and demonstrate reliable, incremental revenue on top of current baselines, it will have a credible story against both legacy incumbents and newer guest-journey suites.
For now, the signal to the market is consolidation around merchandising and the continued push to treat upsell as a program, not a project. Hotels evaluating upsell technology should ask the same questions they always do, with a few added for a post-deal world. What measurable lift did similar properties achieve after fees and over what time period. How quickly can the system go live and what internal resources are required. Which integrations are productized and supported rather than one-off. How the vendor handles guest consent, brand controls and offer fatigue. And finally, how the roadmap will affect current configurations, reporting and commercial terms over the next 12 to 18 months.
While execution will determine outcomes, there is good reason for optimism. Plusgrade brings a large partner network, proven playbooks for always-on experimentation, and experience tying merchandising to loyalty and payments, while Oaky contributes an adoption-friendly workflow and a track record of measurable uplift on pre-arrival and on-property offers. Combining datasets could improve targeting and price-elasticity modeling; shared services across integrations, support and success should shorten time-to-value; and keeping Oaky’s product leadership in a named operating role improves continuity. If the roadmap maintains focus and minimizes disruption for existing customers, the combined platform is well positioned to raise conversion and ancillary capture with less operational lift for hotel teams.
