That experience shaped everything about how I think about sellers. I know what it feels like to be under-equipped in a tough market. I also know what it feels like when something finally clicks, when you find the right approach, have the right conversation, and realize you’re actually good at this.

Gillis exists, in part, because I never wanted talented people to be left to figure it out alone the way I was.

What we’re building now, the technology, the coaching, the culture, is all in service of that same belief. The next generation of hotel sales professionals needs different skills than the last. Comfort with technology. Curiosity about data. The ability to move fast and still be human in the conversation. Those skills can be developed, but only in an environment that actually invests in people.

We’re proud of what our engagement scores and retention numbers say about our culture. But what we’re most proud of is harder to measure: sellers who came in uncertain and are now running portfolios with confidence. Team members who pushed back on how we were building something and made it better. People who chose to grow their careers here when they had other options.

That doesn’t happen because of technology. It happens because of what surrounds it.

If you’re an experienced hotel sales professional looking for that kind of environment, or you know someone who is, we’d love to talk. Not because we’re hiring for a role, but because we’re building something worth being part of.

Reach out at careers@gillissales.com.

The post Why the People Still Come First appeared first on Gillis.

The research time is gone. What used to take 45 minutes per lead, pulling data from multiple systems, cross-referencing signals, figuring out who the right contact was and why the timing made sense, now takes a few minutes. That’s not a small thing. Across a full portfolio of hotels, that’s hours returned to every seller every week.

But what’s happened with that time is the more interesting story.

Our sellers are spending it differently than we anticipated. Yes, they’re making more contacts. But they’re also going deeper into the accounts they were already working. Following up on conversations that used to fall through the cracks because there wasn’t time. Asking better questions because they’re showing up more prepared. Noticing things in accounts that they didn’t have the bandwidth to notice before.

The conversations are changing too. When a seller walks into a call already knowing what’s happening inside an account, the dynamic shifts. They’re not there to gather basic information. They’re there to add to what they already know. Buyers notice that. It’s a different kind of meeting.

AskGillis is doing something we hoped for but weren’t certain about: it’s making newer sellers more confident faster. The coaching is there in the moment, when they need it, not a week later in a training session. We’re seeing them handle objections better, structure their outreach more sharply, and recover from tough calls with more intention.

None of this means the work is easier. The market is competitive and buyers are busy and not every call goes the way you want. But our sellers are better equipped for it than they were six months ago. That’s what we were building toward.

We’re still learning. We’re still iterating. But the early signal is clear: when you remove the friction, people rise.

The post What’s Actually Different Now appeared first on Gillis.

You can build great technology and still lose.

We’ve watched it happen in this industry for years. A new system gets implemented, training happens once, and six months later nobody’s using it the way it was intended. The technology wasn’t the problem. The culture around it was.

That’s why, as we’ve invested in GillisOS and AskGillis, we’ve invested just as hard in the environment our people are working in.

Because tools only amplify what’s already there.

If your culture is reactive, you get faster reaction. If your culture is curious and accountable, you get something much more valuable.

At Gillis, four principles guide how we lead.

Inclusion. The best ideas at Gillis haven’t come from leadership. They’ve come from sellers in the field telling us what wasn’t working, what they needed, and what they were seeing in their accounts that our systems weren’t capturing yet. That input shaped GillisOS in ways no executive could have. When people feel safe saying what’s true, the whole organization gets smarter.

Wellness. Supporting hundreds of hotels across North America is demanding work. The pace has accelerated, not slowed, as we’ve added technology. We’ve had to be intentional about making sure our people have room to breathe, to disconnect, and to bring their full energy to the accounts that need them most. A burned-out seller with a great AI tool is still a burned-out seller.

Growth. We tell our clients that the old sales playbook isn’t enough anymore. We have to mean that internally too. This year our team has had to learn new systems, new workflows, and new ways of thinking about where to focus. That’s uncomfortable. We’ve tried to make it safe to be uncomfortable, because the learning curve is where the growth actually happens.

Purpose. Everything comes back to one belief: there shouldn’t be barriers preventing hotel owners from accessing world-class sales expertise, regardless of the size of their property. That hasn’t changed since day one. What’s changed is how much more we can now do in service of it.

Culture doesn’t make the technology work. But without it, the technology doesn’t stand a chance.

The post What’s Holding It All Together appeared first on Gillis.

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.

The post AI Is Not Replacing Sellers. It Is Replacing Everything Slowing Them Down. appeared first on Gillis.

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.

The post The RFP Process: Shifting from Quantity to Quality appeared first on Gillis.

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.

The post Summer Sales Activity = Fall Revenue appeared first on Gillis.

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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