
Bed & Butter: THE Hospitality Podcast · 2025-03-20 · 25 min
Key moments - from our scoring
Substance score
50 / 100
Five dimensions, 20 points each
Jill Gray brings perspective from multiple hotel environments to her current role at Hampton Inn by Hilton Salem Boston, where the property's location in downtown Salem creates a distinctly different sales dynamic than traditional markets. Unlike most hotel sales roles focused on aggressive quota-hitting, her position demands strategic selectivity - the property can command $700+ nightly rates during peak season (June through October, especially October for Halloween tourism), making it sometimes more profitable to decline wedding groups at $149 rates than to accept them. Her prospecting approach blends old-school community intelligence (driving around, reading local news about company mergers like Johnson & Johnson acquiring ABIOMED) with modern tactics (joining Facebook groups for moms and travel nurses, LinkedIn research, and social media posting). During the COVID opening, she demonstrated resilience by creating unconventional packages and creatively converting guest rooms into meeting and interview spaces for Amazon's warehouse hiring. Gray emphasizes relationship-building as the cornerstone of sustainable sales, supported by detailed organization (BEOs, turndown folders, Outlook file systems) and mentorship from past GMs that she now extends to her team. She advocates for finding genuine passion in hospitality work while maintaining support systems - both corporate and personal - that make the demanding juggling act of career and motherhood manageable.
When a property is selling nightly rates at $700 during peak season and a wedding group wants rooms at $149, accepting the group would displace higher-paying leisure guests, reducing overall revenue. Hampton Inn Salem Boston strategically declines lower-margin groups during high-demand periods to maximize profitability.
A BEO (banquet event order) is a document containing all details for a meeting or group event - including food and beverage setup, billing, parking, and any special requests - that is distributed to the banquet team, front desk, and housekeeping to ensure seamless execution.
Prospecting involves monitoring community activity (reading news about company mergers and acquisitions), driving to observe business developments, joining social media groups relevant to target markets, using LinkedIn to identify key contacts, and continuously researching five new potential clients weekly.
She created unconventional packages like a 'Mom's Night Out' and converted guest rooms into meeting and interview spaces for companies like Amazon; she also made surprise deliveries and leveraged social media to maintain visibility with potential clients.
At Hampton Inn Salem Boston, rather than aggressive quarterly targets, the focus is on strategic bookings that serve the property's overall profitability and reputation, allowing salespeople to prioritize quality relationships over volume metrics.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode contains some practical hotel sales tactics (turning down business during peak seasons, strategic prospecting via social media and online research, creative COVID-era solutions), but much of the content is generic relationship-building advice and motivational anecdotes that would be familiar to any sales professional. The specific insights about Salem's unique leisure market dynamics and revenue management strategy are valuable but limited in scope and depth.
when you're getting $700 a night for a night in October and there's a wedding party that wants the 149 rate, it only makes sense
I try to find five new companies a day, a week, whatever. Learn what I can, see if we can get any business from them
The core advice - build relationships, enjoy what you do, balance work and family through support - represents conventional wisdom in hospitality and sales broadly. While the COVID-era door-knocking and furniture-repurposing examples show some creative problem-solving, the frameworks and takeaways are largely recycled and predictable. The episode lacks contrarian thinking or first-principles analysis.
when you finally get that big group you've been working on, or when a huge account has a group in-house and everything went really well and they thank you
you should definitely enjoy what you do for a living
Jill Gray is a legitimate mid-level hotel sales leader with 10+ years of relevant experience across multiple properties and clear operational responsibility. However, she is not a C-suite executive, founder, or strategic thought leader; she is a skilled practitioner in a narrow role. Her perspective is valuable for aspiring hotel sales professionals but lacks the seniority or cross-functional insight that would elevate this score further.
Director of Sales at Hampton Inn by Hilton Salem Boston
I started working at the front desk. She promoted me to sales manager
The episode includes concrete details about the property (downtown Salem, June - October peak, October Halloween season, $700 vs. $149 nightly rates), specific anecdotes (Amazon hiring project, COVID furniture conversion, four wedding groups scaled back), and named tools (Outlook, legal pads, LinkedIn). However, quantified results are sparse - no mention of booking volume increases, revenue impact of the turned-down business, or measurable outcomes from prospecting efforts. Most claims remain anecdotal rather than data-driven.
we're in a heavy leisure market
when you're getting $700 a night for a night in October
The host asks friendly, open-ended questions and follows up on topics Jill raises (e.g., turning down business, COVID tactics, BEO definitions). However, the questions are largely softball and confirmatory rather than probing or challenging. The host frequently validates and praises Jill without pushing back, testing assumptions, or drilling into trade-offs. There are no moments of productive disagreement or hard questions about strategy limitations or failure.
So we'll get into a few questions. And if you want to go off track and you got something you want to say, feel free
I've heard you mentioned probably in four of these different questions is the word relationship or building relationships. That is the key to your role
Computed from the transcript - who did the talking, and the words that came up most.
Welcome to Season 2 of Bed and Butter, the podcast that takes you into the heart of the hospitality industry. Dive into an engaging episode with Jill Gray, a dynamic sales leader based in the greater Boston area. Discover her unique strategies for building and maintaining relationships, even during challenging times like the pandemic. Jill shares her experiences of balancing a thriving career while being a young mother of twins, highlighting the importance of flexibility and support in the workplace. Her journey offers a glimpse into the varied responsibilities of a hotel salesperson, from collaborating with teams to turning down business for long-term gain. Join us for an inspiring conversation and gain insights into prospecting techniques, the significance of strong relationships, and pivotal moments that shaped her career. Whether you're a budding hospitality professional or looking to refine your expertise, this episode is packed with valuable lessons.
Transcribed and scored by The B2B Podcast Index.
Welcome to Season 2 of Bed and Butter, the hospitality podcast designed exclusively for budding students and aspiring industry leaders. The podcast is in partnership with Southern Maine Community College. We're thrilled to continue this exciting journey with you. Each episode will delve into the heart of hospitality, uncovering invaluable insights, trends, and strategies.
Join us along with culinary professionals, entrepreneurs, hotel and cruise line executives. Whether you're sharpening your skills or stepping into the world of hospitality for the first time, Bed and Butter is your go-to resource. So let's dive in and spread the knowledge one episode at a time. Today, I have the pleasure of introducing one of the most dynamic sales leaders in the greater Boston area, Jill Gray.
With years of experience, Jill has developed invaluable skills in networking, rebuilding relationships, and uncovering hidden business opportunities, even through challenges like the pandemic. As a young mother of twins, Jill also brings a unique perspective on balancing a successful career with family life. Let's enjoy as Jill takes us through the day in the life of a salesperson. So sit back, relax, and get inspired.
Hi, Jill. Boy, I'm excited to have you on this. the podcast today. You've been a joy on the team that you work with, and it's great.
And I wish people could see you smile. I mean, that's the best part of the podcast. I get to see that no one else does. Thanks for joining us.
Thanks so much for having me. That's great. So we'll get into a few questions. And if you want to go off track and you got something you want to say, feel free.
This is really a conversation between two hospitality professionals. So again, thanks for being here. Let's dig into the life of a salesperson, though. What specifically does a hotel salesperson do?
I think most importantly, we build relationships with our clients and the community. Every day is different, but I think most important is connecting with our guests and our clients. I mean, average a day, I think it's important to pay attention to your rivals, see who you have in-house, connect with your groups, connect with your team. Also, continue to prospect, find new business, but make sure the business is right for your property, most importantly.
Well, that's interesting you say that. Why would some business not be right for your property? Well, our property, we're in a heavy leisure market. It's a unique situation because of our location, downtown Salem.
We have so much traffic throughout the year, specifically June through October. Heavily, obviously, in October for all the Halloween pumpkin leggings and crazy business. But we have to be careful. There are some times where we do not want to take groups.
We have to turn them down because we're going to see people pour in leisure guests at the regular rates. and we have to be very careful. I think that's an interesting thing that turning down business can make you more money. That's an interesting concept.
I think I've ever done it at any other property. Well, I mean, I guess you can share. I mean, when you're getting $700 a night for a night in October and there's a wedding party that wants the 149 rate, it only makes sense. And that's interesting.
It's an interesting spot to be in. Whereas in other jobs you've had, it was different. You had to do things differently And how is that different with maybe other jobs you've had in sales? Well, you know, other hotels outside of major cities, you know, smaller towns without as much traffic.
You want to take anything and everything, you know, whatever type of business you can find. And you have a management company that will set these heavy goals quarterly for you to meet. So you become that overly aggressive salesperson that wants to book anything and everything to meet those goals. This is a different situation we have to be more like strategic and what we book and i'm lucky not to have these ridiculous goals set and i had to be very careful and think about the property as entire as an as a whole um i think i think a lot of times people think about hitting their quotas or hitting their their goals and they don't necessarily you have to sell so many rooms you have to sell so many groups or whatever.
And in this case, your goal is really to make the hotel better and more profitable. And how you do it at this hotel might be different than say a big, you know, you worked at a full service, I think you said, and, you know, in a full service, you've got meeting space and you've got contracts and you've got boardrooms and all kinds of things. That is different. How was that transition?
So let's say you came from a big hotel, I think. And what were your, what did you do on a daily basis there? Well, full service, you know, my last hotel, we had a team of about six or seven in our sales and catering department. So I would prospect, get the business, do the contract.
I had a coordinator that would do our group resumes, a convention service manager that would do my BEOs. And my goals were very aggressive. So I had to have that admin team. I couldn't focus on admin tasks.
I had to get that done, get it in, greet the client, make sure everybody's taken care of, and then move on to the next thing, the next booking, and the next prospect. So, yeah, I mean, not to say that we wouldn't be rolling rounds into the ballroom sometimes, but most of the time, my GM wanted my focus on prospecting. Well, you mentioned a few terms in there, and I saw you jotted some notes down, and I'm thinking, shoot, I got to Google this. So, prospecting, what do you consider prospecting?
A little bit of everything. I mean, you're paying attention to what's happening in the community, driving around from looking for piles of dirt to reading the news, making sure, you know, you learn about what companies are being acquired or merged. Or, you know, for example, you want to know that Johnson & Johnson is buying ABIO Med. Now you want to make sure you can find that contact for Johnson & Johnson.
So just really paying attention, digging. I try to find five new companies a day, a week, whatever. Learn what I can, see if we can get any business from them. But if I don't see any opportunity, move on to the next one.
But you know always trying to see what's out there and really just paying attention, let's so there okay so there's one one definition prospecting i just want to see and i think it's great that you're mixing together the old school and the new so the boots on the ground you're driving around and looking for dirt you're looking at cars and parking lots i remember when i started earlier in my career i'd go to other hotels and i'd drive through there and look at any kind of signs on their cars or their reader boards and i'd write notes down one time i had someone chase me out of the parking lot.
I had a person with me and they swore they'd never ride with me again. But I think you're right. I think the prospecting is something that you really got to dig into. But you can do it now, a lot of stuff online and a lot of research.
I think I remember you telling me you've actually gone in to join social media groups of certain kinds of people. I don't remember whether it was wedding people or moms or businesses or something. Moms, moms, travel nurses, everybody talks online. You can join different groups if the admins let you I mean you can post anything on any page until you get kicked off of it it's free advertising it's free exposure it's out there and that's kind of you know if you post the right thing you'll get 50 moms talking about the best place for their hockey team to stay or whatever you know definitely it's there, and then LinkedIn is great for finding that key contact or meeting planner and trying to figure out who that contact is, and then stalking them and then finding them.
You mentioned BEOs. That one didn't come up. I got all kinds of weird things when I put BEO in Google, but what does that mean? I quit event order.
It's all your details for your meeting, food and beverage setup, anything and everything, billing, parking. It goes to your banquet team and your front desk and housekeeping everyone. So it's organizing. And for the record, I did know where BEO was, but I was just having fun with it.
But I think it is critical to have those kind of... The organization goes along. See, not only do you have to be smiley, relationship building, you have to deal with details because you don't want the mother of a bride to come in and have something messed up. I mean, if they wanted their pillow on the left side, not the right side, and it's there, the mother of a bride can let loose.
I know. It's scary. Weddings where you are, but you strategically choose them? Choose who?
Choose when to take them and when not to. Yeah, so that was hard because we opened during COVID. So it was very touch and go. We had our first normal year in 2021, really, and started to ramp up.
And, you know, international travel kind of came back and business travel in 2022. So we finally started to see weekends we were selling out June through October, some stronger than others. And kind of saw like, well, we took three or four groups that weekend. We sold out.
What would happen if we scaled back? So I scaled back on groups the next year, but I took all those inquiries and I saved them to a turndown folder. And then in case as we got closer, we didn't see that demand, so I could reach back out. And luckily, we didn't need them.
So we saw that we were strong without those crazy moms of brides and those wedding groups. And we were selling at rock rate and the demand was there and it benefited us in the long run. and so it's really just. Paying attention, but we did see, for example, last year, 4th of July was not as strong.
There were some softer times during July. So now I keep that in my mind and, you know, we'll take a few here and there. And it's really just being very careful about how we do it and when we take them. So you're not a used car salesman.
You strategically look for the right customer that fits us and we fit them. I think that's, I mean, a lot of times people, when you go in, all they do is just going to do nothing but take anything they can get and, you know, worry about price only. I think you strategically, I think that's a great thing. So let's move a little bit further now into COVID time.
You were a salesperson before. You joined this company and you wondered if you had a job because everything went nuts as soon as you started or just before you started. So how did you, what did you do as a salesperson? You can't knock on doors when we weren't even able to go outside.
What did you do in your sales role then? anything and everything and i created ridiculous packages my mom's night out book a nook come book table in our breakfast room to work remotely and get out of your house anything and everything and i'm i'm grateful that you reached out and told me you thought that was great during those times i appreciated that well we didn't know no one knew the gloves were off it was amazing it was I mean that. And you would call me and say, hey, you're doing a great job.
And I would say, well, I'm not booking anything. And he said, but you're trying and I appreciate that. And that was amazing. Well, I think we don't know that you didn't book anything.
You didn't book anything directly on that package, but someone who might've seen that on social media turned around and became one of your clients or was one of your clients and happened to see that. So I think that's an old thing. And there's two ways, two terms you can use, and I'll use them more, appropriate one um you throw a lot of mud on the wall before some of it sticks. So those that you were just throwing mud at the wall you were doing everything you could but but you did have some clients and you had to deal with them in a different way as well we did and that's kind of the the upside to covet is it made you really think out of the box because we had to and i mean i i wanted i remember i wanted amazon and i couldn't find the right contact and And I literally drove on to the construction site and walked into the guy's trailer, you know, and he put me in touch with the right person.
And he was kind of shocked because there's nobody else on the site but this one project manager in his trailer. And I walked in and it was kind of like and we had masks on and he was shocked. And but anyway, he got me in touch with the right person. That person called me and said, do you have meeting space?
And I said, we do not, but we can make some. Please come by and see what I can do. And we took all the furniture out of a guest room and made it into a meeting room. And we sectioned off furniture in the back of our breakfast room, made that into their hiring, I guess, hiring room or whatever you want to call it, their interviews and applications.
And then they used the guest room, which was a meeting room for drug testing and everything. And for all the new employees they were bringing into their warehouse. Yeah. And then we took that furniture, we put it into our apartment side for travel nurses.
So it kind of was like a full circle thing. So that was kind of cool. Well, what I love is the resilience during that time. and the trying of things.
And I think you said a few things. You walked in and talked to a person. Okay, you were out of the office that day. Another time you snooped around, you did it online.
Another time you just made connections. I think I recall you dropping off things, even though you couldn't go in, dropping off little goodies to some people who weren't even clients yet because we were just barely, we weren't even open yet. Yeah. Like you've delivered them to places during COVID.
Mm-hmm, definitely. I mean, yeah, we did a lot of that. And yeah, it was just a different time. not being able to, you know, be welcome to have meetings with people or just walk into their offices and yeah we would anything and everything you know to just show our appreciation and for any business at that time so it really i feel like it brought you back to that i don't know just appreciating your every piece of business you can get and not that you don't but it really just brought you back there that's the one upside too in that time yeah so what what helps you feel satisfied in your current role?
When you feel, you know, you go home and you feel satisfied. I mean, there's sure there's days you go home that I'm like, what the heck am I doing in this business? But what satisfies you? What makes you like, wow, I'm excited.
It's cheesy and simple, but when you finally get that big group you've been working on, or when a huge account has a group in-house and everything went really well and they thank you and they thank your team, even better, they give your team a gratuity. That's even feels even better because thank your team because they're the reason that they're coming back they're the reason that they're happy and everything went well that's great and i don't think that's cheesy at all i think that's you know what what excites people everybody has their own hot buttons and what it what it is some people might be the book in the room some people might be the relationship but i've heard you mentioned probably in four of these different questions is the word relationship or building relationships.
That is the key to your role. And it's not, you know, the used car salesman might not have a relationship with you other than they sell you a car, but you're in it for the long haul. You want rooms today, you want them next week, and you want them next year. And I think that's admirable.
And I think, I hope the listeners heard that because I've heard that whole thing about relationship with you. That's really great. Now, there must have been someone along your career that really made an impact and how it It made things a little, it kind of stuck in your mind and it made you feel good and it made you feel like you want to do more. Have you got a certain person that maybe did that for you?
I would say a couple of my past GMs. One would be my first GM ever. I'm still in touch with her in San Diego. She, that was a hotel.
I started working at the front desk. She promoted me to sales manager. I was helping out and that's kind of the start of my career. And she's amazing.
and she kind of took me in and took care of me and taught me so much. So definitely her, another GM in Brookline, I went through a hotel opening. She was amazing. That's great.
And I think when you're working with other people, you remember that and you kind of want to do the same thing for them. You want to help someone else on your team. And I see you working side by side with people at the desk or I see you going down the halls and talking to housekeeping. The things that you learned from those GMs is probably some of that.
And maybe you would have done it anyway but they just reinforce the need for that and I think that's what hospitality is about it's not just being hospitable to our guests but also to our associates because the associates take care of the guests and then they just keep going absolutely. So, you know, I've really admired you, and I really do mean this as a person. I've admired you as a salesperson as well, or at least over the last few years. Tell me how you balance life with a family.
You have twins, seven-and-a-half-year-old twins. Yes. And you're a mom, and you do stuff in the community, and you're a sales professional, and sometimes you're running around talking to housekeepers, you're talking to brides and bridesmothers. How do you balance all that or is there is it balance or is this something else how do you how do you get through that i don't think you can balance it there's no balance it's never balance, it's it's it's hard and you just you everybody always says like you always read those memes online and all that other everybody wants to have the perfect balance and i think with kids and work it's impossible it's it's not you just take a deep breath do the best you can but i'm lucky that, and I mean this, I'm lucky that I have a lot of support.
I do feel that support from main course, from my GM. If I have to leave work for somebody sick at school at two or whatever, I feel supported. So once the kids are in bed, I don't mind opening up my laptop at eight o'clock at night, you know, and seeing if I got that group or sending out that contract or whatever. When you feel supported and like who you work for, it doesn't feel like a burden or anything.
Like you can carry all of it. I don't know. You can carry all of it better if that's, I don't know how I want to say that. But if you have that person you work for, it makes the balance feel more manageable.
And I think that's a two-way thing. Yes, you have supportive leaders and you have a supportive company. But it's also you're showing quality work and putting in your time and doing your work. And it's really just that you earned the time to be able to spend with the two kids or one kid.
It's probably easier one at a time than two at a time. But, you know, and I think, you know, it's supporting the family. I think that our, not just the world, but I think the world, our industry and our company culture has evolved into that. I think that's a real important thing because, and I'm on the other end of my career, but I still believe that that's what's going to set us apart is if we can make sure we do that right.
Get the work done, get the people we have, but also give some light, let people have a life. So I'm glad that you feel that way about your boss and your company. I also want to say, I think it's important to like what you do, you know? It doesn't feel like you're working.
That's so important to love what you do, and that makes it much easier also. What would you, what's important to you in your life? My kids. Yeah.
My family. Helping people. Sorry, I think that's great. If you can, if you've got your kids and you've got your husband and the rest of your family and you care about people.
And I think the caring, I mean, family is, you've got your family at home, but you've also got extended family. You've got your work family. And I think you mentioned caring. And I think what happens is the guests can feel that.
And it goes right back to the same thing. We take care of our families and our guests and our associates, and the guests are going to keep coming back. Then we'll all make more money. And that's a good thing.
Yeah. And we'll all do better and we have a better career. So that's great. I'm glad that's important.
I'm glad you're able to find a way to maybe not balance, but just not get too off kilter with one versus taking over the other. I think that's great. Now, this is a crazy question. Do you have certain success habits, like things you must do because that's what makes you more successful?
Things i maybe i how you organize or how you start your day or how you end your day or those kinds of things or anything that really helps you get through all of you've got to do i'm old school i like my legal steno pad and before i end the day i write out what i need to do my priorities and i prioritize them prioritize them for the next day any notes or whatever reminders if i'm out on sales calls i just plug it into my phone i love my outlook i I mean, that's obviously, I have a file for every company and anything and everything.
I love the idea where you, at the end of the day, you go over what's on your pad and then, yeah, it might be old school, but it's like, it's really organized. And you say, okay, now what do I have to prioritize for the next day? I mean, I think that's awesome. I have another DOS, which I'm trying to start doing it again, but she would write down five companies at the end of the day that she wants to look at the next morning, spend a couple minutes on each company, literally the first hour of the next day, see if there's anything there and move on.
And that's it. It's really quick, simple. That's something I'm trying to do again. Well, I hope there's not any listeners that are around your hotel, but I think that's a great idea.
Okay, you've been around for a while. I mean, you're not just out of college, but you're not on my end of the spectrum. Okay. How about giving some advice?
We've got some hospitality leaders that are out there. They could be students. They could be young professionals in our business. And there's people at Hilton America.
Give a chance to help them, you know, say something to them, some kind of advice. Uh really pay attention to you know see i don't know which which department you identify with the best um if it's operations or sales i feel like everybody's kind of like one or the other they feel more strongly about definitely follow your heart and which which one you choose um because again i like i had said before i think it's you're gonna do well if you love what you do And then, you know, that old school saying, you know, work a day in your life if you enjoy your, you know, what you do for work.
And that's just so important. I mean, that's the majority of your time is spent during your work week. I mean, you should definitely enjoy what you do for a living. So I think just follow your heart and pay attention to what makes you happy.
That's great. I think, you know, and you can say, I know you're thinking that could be cheesy. It's not cheesy. I can see you laughing now.
It's not, though. You really do have to enjoy what you're doing. I mean, I come into that hotel and visit, and you're bubbly, you're happy, you're having a good time, and then you're joking around with your boss. And that just creates an environment where if you walk out into the lobby at that point, you've got a big smile on your face.
And guests are going to be happier, and so are the associates. So as cheesy as I know you're shaking your head and laughing about it is, it's real. It's a real thing. And that's why your core values in your company is that fun is one of them.
Yeah, I think that's the best part about the hotel industry. You don't know who's going to walk through the door. You're going to have so many guests from so many different backgrounds and companies and groups and associations. And that's a great thing.
You're not sitting in a cubicle in some huge call center or doing accounting somewhere. Every day is different and you get to meet all these different people with different backgrounds and learn from them. So that's another thing that I feel like is kind of cool about the hotel industry. So from this discussion we've had, I've learned a little bit about you and your life.
I've learned about what makes you successful. And I think for our listeners to hear that, it's great. I've learned some new terms. And I think that's really great for younger folks that are joining this to learn those things.
And I've enjoyed listening to you talk about how you go after business, how you get it, and then how you keep it by taking care of them. So I'm just summarizing because I'm so impressed with all that was said today without a whole lot of planning other than that's just inside of you. And you sharing that now with listeners of hundreds and hundreds, maybe thousands of people that are maybe thinking of being in a sales position. So Jill, I can't tell you how much I appreciate you being here.
You've really been great for myself, but I know you are for our listeners. And thank you for being part of this with me. Well, thank you so much for having me. Thank you for joining us for another episode of Bed and Butter, the hospitality podcast produced in partnership with Southern Maine Community College.
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