Introducing GillisOS + AskGillis.

We are excited to officially introduce GillisOS and AskGillis.

This is not a generic prospecting tool or a traditional training program. It is a purpose-built system designed for how hotel sales actually works, account by account and project by project.

GillisOS continuously scans the market and surfaces real buying signals at a scale no human could process. It connects fragmented data into a single view of demand and highlights where sellers should focus.

AskGillis is the coaching layer built on the same methodology we train our teams on every day. It guides sellers in the flow of work, helping them translate insight into relevant outreach, stronger conversations, and better outcomes.
Together, this changes how our teams work.

For our employees, it removes hours of manual research and gives them clarity on where to focus. It supports them with just in time coaching so they can show up with confidence and consistency.

For our clients, it means more targeted prospecting, stronger account penetration, and a more efficient path to revenue.

For our industry, it signals a shift. Hotel sales is moving from manual, reactive work to a more intelligent, insight driven model.

At Gillis, our mission has always been simple: to make sales accessible and achievable for all hotel owners. GillisOS and AskGillis are the next evolution of that commitment, helping sales teams work smarter, focus on the right opportunities, and drive stronger results.

Whether you’re a hotel owner, management company, sales leader, or industry partner, we’d love to show you how these innovations are helping transform hotel sales.

To learn more about our approach or explore how we can support your business, contact us at sales@gillissales.com.

Modern selling is here. We are proud to be building what comes next.

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AI Is Not Replacing Sellers. It is Replacing Everything Slowing Them Down.

For years, hotel sellers have been stuck doing work that does not move revenue. Researching accounts. Searching for contacts. Trying to piece together what is happening in a market.

AI changes that.

Today, AI can identify companies that are traveling, surface decision makers, and generate relevant outreach based on real signals. It can do in minutes what used to take hours.

This is not about sending mass emails. That was automation. This is different.

This is about enabling sellers to show up informed, relevant, and prepared. It increases their capacity without increasing headcount. It gives them time back to focus on what actually drives revenue, building relationships and closing business.

The role of the seller is not going away. It is evolving.

The best sellers will use AI to move faster, go deeper into accounts, and spend more time where it matters. Those who do will outperform.

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So how do you rise above the noise?

You don’t beg for attention – you earn it.

Sellers who consistently land meetings aren’t the ones sending more emails. They’re the ones showing up with relevance, insight, and genuine value – the kind that’s tailored, thoughtful, and impossible to ignore.

Here are 3 strategies to help you jump the queue and stand out to your buyers:

1. Be Relevant.

Generic messaging doesn’t cut it anymore. If your outreach could be sent it anyone, it will resonate with no one. Tailor your message to what matters to them – their role, industry, recent changes, or strategic initiatives.

• Lead with their priorities, not your pitch.
• Reference something timely: a product launch, funding round, or expansion project.
• Keep it short, specific, and use their language not, hotel speak.

2. Do Your Homework.

Sellers at Gillis aren’t just persistent – they’re prepared. Do the digging that most won’t: review prospect’s websites, job postings, press coverage, and reviews. Understand their goals, challenges, and context. People notice when you’ve done your research. More importantly, they respond.

• Mention competitor activity or market shifts.
• Bring up internal initiatives or role-specific pressures.
• Use LinkedIn activity to tailor messaging (e.g., “I saw your post… here’s something that might help”).

3. Show Up with More Value.

The fastest way to grab your prospect’s attention is to bring insight they don’t already have. Don’t pitch-slap – start a smarter conversation. Value builds trust and trust opens doors.

• Share industry benchmarks, added value, or trend analysis.
• Send a short, personalized video or voice note explaining how you can help.
• Meet them where they are at in their buying process and keep in touch as their needs evolve.

Today’s buyers don’t need more follow-ups – they need more relevance. If you want to jump the line and stand out, bring something worth stopping for – and for even more actionable strategies to elevate your sales game, grab a copy of Tammy’s “Room to Grow” and keep growing your impact.

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Our CEO & Founder, Tammy Gillis recently called out the need for change in a post on LinkedIn. “The [RFP] process desperately needs to evolve” and simply being listed doesn’t guarantee business. So where do we go from here?

Time to Rethink the Playbook

The hospitality industry is rapidly evolving. AI is reshaping how we forecast and respond to demand. Distribution platforms are multiplying. And today’s traveler can book through dozens of different channels.  It’s time consuming and outdated.

Shifting from Quantity to Quality

Rather than chasing every RFP, sellers need to take a more strategic approach:

• Prioritize fit over volume – focus on RFPs that align with your location, amenities, rate strategy, and service level.
• Use data to your advantage – understand which accounts converted last year and why.
• Collaborate across departments – revenue and marketing teams should help evaluate which RFPs support your broader business goals.
• Activation is Key – a “Set it and Forget it” strategy doesn’t work. Engage with local and regional offices of your preferred accounts to shift share.

 Embrace Change Before it Leaves You Behind

The future of corporate travel sourcing is uncertain and platforms like Navan and Spotnana are already reshaping how business travel is sourced and booked. These tools may eventually bypass legacy RFP systems altogether – are we ready?

If hotel sales teams want to stay relevant, we must rethink how we approach RFP season. It’s no longer just about being “on the shelf” – it’s about standing out when and where the customer is making decisions.

What You Can Do Now

• Re-evaluate your RFP strategy with your commercial team.
• Say “no” more often to opportunities that don’t fit.
• Start conversations internally about how to streamline efforts and measure results more effectively.

RFP season doesn’t have to feel endless or uncertain – it can be a strategic advantage when you pursue what truly drives your results. At Gillis Sales, we help hotels navigate this complexity with focus, clarity, and confidence. From evaluating opportunities to building smarter sales strategies, we’re here to be your trusted advisor every step of the way. Let’s stop treating RFPs as a checkbox and start turning them into a catalyst for growth.

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If you’re not carving out time for sales now, you’re setting yourself up for a dry pipeline this fall.

Sales is not a tap you turn on when things slow down. It’s a long game – a relationship game. And the seeds you plant in July will grow into business in Q4 and Q1. The momentum you build now is what sets you apart later.

That’s why at Gillis we’re reminding our partners: Sales can’t take a backseat to operations. Not even during the summer surge.

Ask yourself:

• Are we reconnecting with our key accounts before someone else does?
• Are we actively identifying new business in the market – beyond just inbound leads?
• Are we paying attention to what’s staying at our comp set?

If you answered “not really” to any of these, it’s time to shift gears. Sales doesn’t stop when guests check in. In fact, that’s when your future revenue is won or lost.

At Gillis, we specialize in helping hotel teams stay proactive even during their busiest seasons. Because when the rush ends, you don’t want to start from zero.

Five simple yet powerful ways to keep the sales engine running in peak season:

• Time-Block Prospecting Daily – treat this space like a meeting you can’t skip. Small, consistent efforts will move the needle forward.
• Use Call Sheets – Plan out your calls ahead of your designated prospecting time. Focus on key accounts, lapsed clients, and new leads.
• Automate Where You Can – Set up email reminders and templates. Make tech work for you when time is limited.
• Share the Load – Empower front desk or operations staff with quick training to flag potential leads. Everyone can help drive revenue.
• Celebrate Small Wins – Closed business is great – but celebrate reconnected accounts, booked appointments, and sent proposals. Momentum matters.

Stay focused. Stay selling. Your future self will thank you.

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I did a live demo of some sales use cases during a recent online seminar and it’s fascinating the potential this has to save time while providing great intel.

The quality of the prompt that you put in will dictate the quality of the reply that ChatGPT returns. And it’s an iterative process. The more information you feed it, the smarter and more concise it becomes.

Below are some prompts that you can try out to get started:

Prompt #1

• Write a prospecting email from a hotel sales manager’s perspective to an admin assistant of a local company who is using a competitive hotel for their lodging needs

Prompt #2

• What are the biggest companies with hotel needs in (insert city)? b) What employers have offices throughout the United States?

Prompt #3

• What sports tournaments take place in (insert city)?
• What hotels are listed are host hotels for these tournaments?

Prompt #4

• Create a training plan for a new hotel sales manager
• Focus on prospecting skills

Prompt #5

• What government contractors sell to military bases?
• What travel agencies book their travel?

Don’t be afraid to get started. Jump in with some of these prompts and let us know what you valued most!

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And what is the difference between each dimension?

The difference between each dimension is the research conducted ahead of time by the seller and how it’s leveraged to have a business conversation vs. a sales conversation.

If you can picture a 1D object i.e.: a straight line, it is flat and lacks depth and complexity. Many prospecting emails lack depth and complexity and sound like this:

“I am wondering if you are the person in charge of booking hotels in our area. We are interested in providing rates for your company and would like to partner with you in the coming year.”

A 2D object like a square, has shape and shows length and width. A 2D sales approach demonstrates some thought but not enough to motivate the buyer to respond. It sounds something like:

“I understand your company has business in our area and given our proximity to your job site, along with our newly renovated rooms and free breakfast, we feel we would be a good fit.”

An example of a 3D object is a cube which has both breadth and depth. In my experience, very few emails are written from this perspective.

If sellers want to rise above the noise and cut through all the clutter that a buyer has to sift through in a day, they need to have breadth and depth in their sales execution.

A 3D sales approach would sound something like this:

“Congratulations on being awarded the bridge rehabilitation project in ABC town. We’ve had the pleasure of hosting Bobby Smith and Suzy Keller while they have been in town working on the initial phase of the project.

We understand from Bobby and Suzy that construction will begin in the next 90 days and you will be bringing in out-of-town contractors for the project.

Given the many things you have on your plate, we would be happy to put together accommodation recommendations and provide your crew with a home away from home experience.

We have extensive experience taking care of clients who are away from home for an extended period. They appreciate our well-lit truck parking, our rooms with kitchenettes, and our complimentary hot breakfast that is available at 5:30 am.

Are you available this week to further discuss how I can take care of this part of your project for you?”

As sales teams and leaders look ahead to the rest of the year, it’s important to know what good looks like when it comes to sales execution.

It’s the difference between playing chess or checkers.

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Consider for a moment a salesperson or a sales director executing sales pre covid?

What might they tell you about their experience in sales?

They’d likely talk about how successful they were. During a time of unprecedented growth in the industry, they were able to meet their revenue targets. They grew their accounts by staying connected with clients and being personable and available to respond to incoming inquiries. But ask yourself: Did they ever have the experience of making call after call without the instant gratification that comes from hearing “yes”?

Today’s sales realities mean that the salesperson you hired 10 years ago is probably not the salesperson you need today. Building a sales team and not leaving sales to chance means that your hires have to be effective and skilled at selling regardless of shifts in the market or new competitors, and they need to be able to have a business conversation with an informed buyer.

What kind of sales team do you need?

The size and structure of your sales team are determined by a number of factors. Start by looking at your hotel segment and number of rooms—economy, mid-scale, select service, full service—your brand, size of market, and demand generators in your area. For example, a hotel located in a tier-one market with 500 rooms and 20,000 square feet of meeting space is going to need a different sales structure than an 80-room Holiday Inn Express in a secondary market. If you are an independent hotel with no brand support, you will need to invest in some level of  sales support.

And don’t expect hunters to be farmers, or vice versa. Hunters get their energy through  pursuing new opportunities. They have a lot of initiative and are not easily discouraged. They are competitive and high achievers. Farmers are more focused on developing relationships. They are the nurturers who want to provide a high degree of customer service. They enjoy the busy details that come with putting together contracts and banquet event orders (BEO s).

Most salespeople do a bit of both—incoming inquiry management and new business  development—but in general, if someone is good at one, they should lean into those strengths. Don’t expect a lead catcher (a farmer) to be good at hunting for new business. And if you constrain a hunter to a desk job managing wedding blocks and administrative tasks, they will likely leave as soon as something more interesting comes their way.

One of the pain points I often hear from clients is their frustration with finding and maintaining sales talent. They hire candidates who look good on paper and have experience, or they hire someone with less experience who they feel is coachable. But within six months to a year, the owner does not see the results, the salesperson either leaves or is terminated, and the process starts again. These are symptoms of bigger challenges, and in our industry and in my experience, there are three key areas that need an overhaul if we want to reduce the high turnover:

1.  Many hotel owners don’t know what they are looking for (i.e., what “good” looks like) because many don’t have a sales background and don’t know how to screen for the right candidate.
2.  Too many organizations don’t have the sales infrastructure in place to support this role once the salesperson is onboard. They assume that if they hire experienced salespeople, they will know what to do.
3.  Outdated hiring practices. Now more than ever, sales professionals are looking for work/life balance. Many are tired of working on property and getting pulled into operations. They are looking for hybrid or remote positions that afford them the flexibility that other industries offer. They also value training, coaching and support, which the hotel industry does not consistently do well.

Vacant sales positions impact revenue and so does employee turnover. Take the time to consider what you are looking for and ensure you have the job description that fits that role profile along with an  internal support system to coach, develop and measure your sales team.

The post Knowing What Good Looks Like appeared first on Gillis.

In our experience, when clients first engage with us to help them with their sales strategy, they are typically over indexing in OTA reservations and lacking  corporate base business. They tend to do well on weekends with leisure, sports teams and events; however, they are not getting their fair share of the B2B weekday business.  In the absence of a sales strategy, this is a common problem that has real consequences for the success of a hotel and its profitability.

Costs for client acquisition are rising and more owners, operators and sales teams are paying attention to profit, not just top line revenue. The success of a hotel’s commercial strategy (sales, digital marketing, revenue and distribution) is getting the best mix of business that is profitable across all channels. According to Kalibri Labs, an OTA reservation on average is $12 more per room compared to loyalty member rates.

When it comes to corporate travel post pandemic, there has been a major shift in who is traveling. The fortune 1000 companies that made up the bulk of the demand pre pandemic are not the companies driving the demand today. The companies driving the corporate market today are local and regional accounts. They are largely unmanaged accounts. Meaning, not part of a large managed hotel program booking through a travel management company and having a formal RFP process. These travelers are typically not using the GDS to book and are booking through digital channels and direct to the hotel.

Hotel teams and brands need to rethink their legacy sales structures to adapt to these corporate buying trends. Relationships with local and regional companies are more important than ever before while staying on top of local demands generators.

According to Kalibri Labs 2022 Special Report, in every prior industry recovery cycle, revenue growth was driven by occupancy growth with ADR following later. The current recovery is just the opposite, with ADR growth leading the way and demand lagging.  In other words, demand isn’t growing, hotels have to go and shift it way from their competitors to successfully compete.

In summary, it’s not enough for hotels to simply have “rates on the shelf” with various companies and hope travelers will book. Getting on the shelf is the starting line. It’s critical that hotel teams have a strategy to target the right customers while activating the local and regional accounts in their backyard. Hotel teams that figure this out will be the ones that come out on top.

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Discover the delightful taste of summer with the Gillis Family’s cherished pineapple square recipe. Bursting with tropical flavor and a touch of nostalgia, these pineapple squares are a perfect treat for sunny days and warm gatherings. Simple to make and refreshingly delicious, this family favorite is sure to become a staple at your summer celebrations.

Crust

• 1 ½ cup graham cracker crumbs
• 6 tablespoons butter, melted
• 1/3 cup of white sugar

Topping

• 1 8 oz brick of cream cheese
• ½ cup white sugar
• 15 oz can of crushed pineapple, drained well
• 1 tub of cool whip

Instructions

For the Crust

1. In a mixing bowl, mix the graham cracker crumbs and sugar.
2. Make a well in the center and mix in the melted butter.
3. Press into a 9×9” baking pan. Set aside.

For the Filling

1. In a stand mixer, beat together the cream cheese and sugar.
2. Then add the crushed pineapple until just incorporated.
3. With a spatula, fold in the cool whip until just mixed.
4. Pour mixture on top of the crust.
5. Cover and place in the refrigerator for at least 2 hours to set.
6. Cut, Serve and Enjoy!

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