Turn Your Data into Dollars: Grow your Outbound Sales Through Your Customer Data

Resources
Great WISE blog on managing a phone team: https://wineindustrysaleseducation.com/managing-an-outbound-calling-program/

Key Phone Skills for Success - https://wineindustrysaleseducation.com/key-phone-skills-for-success/

Managing an Outbound Calling Program - https://wineindustrysaleseducation.com/managing-an-outbound-calling-program/

Outsourcing Telesales - https://wineindustrysaleseducation.com/outsourcing-telesales/
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Turn Your Data into Dollars: Grow Your Outbound Sales Through Your Customer Data

Webinar Transcript — March 19, 2026

Participants:

Cathy Huyghe: All right, everyone — thank you so much for being here. Thank you to Robert, Jennifer, and Ben for your time in preparation for this conversation, and for being willing to share your expertise and years of experience. Chris and I are very happy to see everyone and to see the interest in this topic — turning data into dollars, with a particular focus today on outbound sales.

We're going to jump in. Ben Wright, Outbound Sales Manager from Plumpjack. Jennifer Warrington — "The Glue," I love that — from WISE Wine Industry Sales Education. And Robert Breedlove, DTC Specialist at Alpha Omega. So much experience at the table right now.

As we were preparing for this, I literally said out loud, "We should have just recorded the prep call," because that is the gold we want to communicate today.

So let's jump in with the most basic question: What does an outbound sales department do? And as a sub-question — how does it support other departments at the winery? Let's start with the educational component. Ben, what does an outbound sales department do?

Ben Wright: Our outbound sales department at Plumpjack manages the Plumpjack, Cade, and Odette brands. Each of my team members has about 1,000 assigned customers. They create lists based on our sales focus — new releases, last calls, featured library wines, winemaker dinners, special occasions, and our biggest event: corporate gifting in November and December, which is a big boost for the department.

We also answer inbound calls — instead of going to the tasting room, they come into our office. We make tasting room reservations, follow up on tasting room visitors to see how they enjoyed their experience, follow up on completed web orders as well as abandoned carts, and manage shipping and logistics — weather holds, misdeliveries, returns, et cetera. I think the question is, what don't we do?

Cathy Huyghe: Yeah, for sure. And as we were listening to that list, Ben, you're touching so many different parts of the winery. I wanted to kick it over to Jenn to say a little more about that.

Jenn Warrington: Great point. Our customers have one relationship with the winery, and yet oftentimes we get so in our own bubble that we think, "Wine club — this is my customer. Tasting room — this is my customer. Outbound phone sales — this is my customer." But the guest only understands that it's one winery. I loved how Ben described supporting so many other departments — it's about helping all the departments work together. It's part of a bigger ecosystem.

Cathy Huyghe: Yeah, and something you said, Jenn — the relationship is with the winery.

Jenn Warrington: Yes, absolutely. They don't know the difference, and why would they — or why should they?

Cathy Huyghe: So important. Robert, what's your take?

Robert Breedlove: I think Ben brought up a good point with "what don't we do?" It's very much a Swiss Army knife position — handling inquiries, obviously making outbound sales as the name suggests, but basically trying to be a one-stop shop for anything a guest could need. You have to be adaptable. One call that comes in might be a fulfillment redirect, and the very next could be someone wanting to make changes to their upcoming club shipment. It covers a lot and touches on pretty much every department.

Cathy Huyghe: I love that point about the Swiss Army knife, Robert. That's really important. Moving on — let's talk about profitability. Is it worth it? And Jenn, you made an important point: is it worth it not to do it?

Jenn Warrington: Absolutely. People drink wine all year round — isn't it in our best interest to be selling to them all year round, and in different ways? People want to interact with us as a winery in different ways — whether that's a phone call, a text, or an email. There's so much opportunity in outbound phone sales.

Community Benchmark has about 5,000 wineries on their platform, all on the West Coast, and what they're seeing is that the wineries doing well — the top 20% that are beating trends by more than 20% of breakeven — are up 26% in phone sales, and their AOV is up 20%.

Commerce 7 also did a data drop just yesterday showing that the phone sales channel represents about 13% of their overall DTC volume.

What we're seeing is: when tasting room traffic is down, the wineries that are winning are leaning into outbound phone sales, text messaging, and in-market events. What's old is new again, and there's a huge opportunity. So many wineries don't utilize it because they think it's cold calling — and it really isn't. Their customers already like the brand, so they're already warm.

Cathy Huyghe: And Jenn, this is a very interesting one — tele-sales definitely outperforms the other channels in AOV.

Jenn Warrington: Yes, because people buy by the case quite often. When we were doing monthly reporting with WineDirect, the tele-sales channel was always, by far, the most revenue-generating channel.

People aren't going to multiple wineries in a day — they're talking to you. You're hand-holding them, helping them figure out what they want, so it becomes a natural, easy way to drive lots of sales. Even if the intended call is just to check in and see how their last club shipment was, there's always an opportunity there to continue building the relationship.

Cathy Huyghe: Ben, you made an important point about outbound sales in relation to foot traffic — and specifically to Napa, and how expensive it has become to spend a weekend there. Can you say a little more about that?

Ben Wright: Absolutely. It's that extended relationship. People come to Napa realistically maybe once a year — if we're lucky. Back in 2022, everybody was going to Europe, so they weren't coming to Napa. Visitation was down. Hotels were $500+ a night. So if you're only coming to Napa once every few years, where are you getting your wine during all that time in between? That's where we get to extend the relationship and build it. And it works both ways — when those customers come back to Napa two or three years later, they're coming to the wineries they've built a relationship with.

Cathy Huyghe: It was really enlightening, as we were preparing, how much more important outbound sales teams are than I think they get credit for. So how do we build one? Ben, you mentioned that the origin of Plumpjack's outbound sales team was during 2020, as a way for salespeople to keep making money. Can you say a little more about that?

Ben Wright: In 2020, there was a sudden decline in tasting room visitation, and we had wine educators who needed to work — and we had wine we needed to sell. The obvious solution was to create an outbound sales team. It started with a few people calling club members and customers who had canceled reservations because of the pandemic. Then it became us calling people in our database and touching base with customers who had placed website orders. As the tasting room started to open up again, we still had success in outbound sales and grew the team from four people to seven over the past three years. It gives our customers a point of contact at the winery — someone they can trust to talk about wine and be their Napa Valley insider when they can't come visit.

Cathy Huyghe: And what's exciting about your program, Ben, is how you've divided your customer database among your salespeople — each person is responsible for cultivating a specific group. I think that's a great model. Robert, you made the point that it's not that everybody has this all figured out from the beginning — what matters most is to just start.

Robert Breedlove: Absolutely. If you look at what Ben and I have built and you're starting from nothing, it can look daunting — like you have to go find four or five people right away. But it doesn't have to be a moon launch. Let it grow organically. Ben's program grew out of a real need and expanded from there. The same thing happened with us — we started before COVID, but it got a big boost during the pandemic. Letting it grow organically and become what it's meant to become is the right approach.

Cathy Huyghe: Jenn, going back to something you said earlier — why wouldn't you do this?

Jenn Warrington: A lot of it has to do with the size of your database — if you have a smaller one, you'd need a smaller team or fewer resources. But if we're not reaching out to the guests and customers who already love us, it becomes transactional. We're just waiting for them to buy. If you create a program where you're actively reaching out and touching base, it's a win-win — you're growing engagement and generating potential sales.

In terms of the financials, you need to think about labor costs, ROI, and compensation. Best practice is to pay outbound callers a bit more than a straight salary because it's different from working the tasting room — they're not getting tips, and selling on the phone is harder. Offering between 2% and 6% commission depending on your financials is a reasonable starting point. You also need to think about who's making the calls, what metrics you'll track, what the incentives are — but it doesn't have to be overwhelming.

At the very least, if you're picking up the phone and talking to the people who love you most — your wine club members, your top buyers — that's an easy place to start.

Cathy Huyghe: And to your point, Jenn — you don't need to create a dedicated outbound sales department to do outbound sales. Not every winery will be able to do that.

Jenn Warrington: True. And at the same time, when we think about the skills required, I wouldn't necessarily recommend pulling someone off the tasting room floor. Being good at in-person sales doesn't automatically translate to phone sales. If someone is going to be doing outbound calling for any period of time, we highly recommend setting aside four dedicated hours — it takes time to figure out who you're going to call, what the offer is, and get into the right mindset. If you're getting pulled in different directions, it's not going to be effective.

Cathy Huyghe: WISE recommends a dedicated window of time — not popping in from the tasting room floor to make a quick call and then heading back. Focus and consistency matter.

And WISE has a great resource on this — "Five Key Phone Skills for Success" — worth looking into.

Cathy Huyghe: A question came in: what channel appears to be trending more — outbound sales or e-commerce?

Cathy Huyghe: From what we've seen — maybe not overall revenue, but definitely AOV — it's clearly outbound sales.

Jenn Warrington: I'd agree with that as well.

Cathy Huyghe: Ben, what skills do you look for in outbound salespeople?

Ben Wright: The first is persistence. Just getting in every day, building those relationships, making the calls. You're going to get a lot of voicemails — and now that iPhones can hang up mid-voicemail, that happens too. But if you're persistent, you're going to reach that customer at exactly the right moment.

They also need marketing aptitude — you're talking about products, events, creating emails, sending text messages. Objection handling is critical, because when you're asking someone to spend a couple thousand dollars, they're going to push back. And being methodical about note-taking is huge, so that when you call that customer a month or two later, you know what the last conversation was, what they purchased, and what motivates them.

Last but not least — long-term commitment. You can't build real relationships on seasonal employees. The hardest thing for our department is turnover. When you lose someone who's been nurturing a relationship with a customer for years, you're starting over. You need people who are committed to the brand for the long haul.

Cathy Huyghe: Longevity and consistency — knowing that this is your role, you show up, and this is what you do.

Cathy Huyghe: And it can also be a career path — someone who's worked in the tasting room, knows the winery well, and has the right skills can grow into this role. Also, a quick comment from Eric in the chat: for established members with an address and card on file, an order for a case of their favorite wine can take as little as two minutes. It creates repeat buyers without requiring a lengthy process — and as we've said, it often goes by the case.

Jenn Warrington: I was also thinking about the emotional side of it — you get a lot of "no." Or worse, silence. It has to be someone who doesn't take that personally and is willing to keep picking up the phone. You have to try many times before you actually connect with someone, and even then, not every connection leads to a sale. It's got to be the right personality. And honestly — it needs to be people who actually want to talk on the phone. Some generations are just more comfortable with a text, and that's worth thinking through when you're hiring.

Cathy Huyghe: Robert, both Ben and Jenn have touched on the thick-skin component. What's been your experience?

Robert Breedlove: In any sales role you have to be prepared to hear "no," but what's different here is getting used to hearing nothing — sometimes for long stretches. You're calling people who are out living their lives. You might catch them at work, you might get their voicemail, you might get several voicemails in a row as you work through a list. The determination and willingness to put in the work is everything — it's a numbers game.

But the calls do come back. Someone sees your voicemail a few days later and calls back: "Hey, I've been meaning to order X, Y, Z." You also have to be adaptable — once you have someone on the phone, the conversation can go anywhere. They might have a question about a recent shipment, so being able to think on your feet is really important.

Cathy Huyghe: I love that point about getting the reps in, Robert. We talk about that in exercise all the time — just show up, make the call, send the email, get the reps in. That's how you get to the next sale.

Robert Breedlove: And taking good notes as you go. If you've tried calling someone every Tuesday at 9am and they're never available, try a different time. Good notes turn it all into one long conversation rather than a series of disconnected ones.

Cathy Huyghe: Shifting to setting goals and managing an outbound sales team — Ben, how do you set goals? What are you measuring?

Ben Wright: We have monthly financial goals for the department, but we also have outbound activity goals. We make sure the team is calling a set number of people every day and every month. Same with outbound emails — sometimes people unsubscribe to marketing emails, but a personal email is different. As long as it's authentic and makes a genuine connection, people aren't going to unsubscribe to that. So making those calls and sending those personal emails — that counts as success too.

Cathy Huyghe: Jenn, you and WISE have some resources on KPIs and key metrics to track. Can you share some of those?

Jenn Warrington: Absolutely — I'll drop some in the chat. But yes: if you're not measuring it, you don't know if you're successful. Measure what matters. Start with how many calls are made, how many result in actual right-party contact, of those connected how many converted, what was the overall sales figure — things like that. I have a couple of resources to share: a simple daily tracker for the person making calls, and an Excel spreadsheet for managers who want to roll up all those metrics and analyze them. Helpful especially for smaller or mid-sized wineries just getting started.

Cathy Huyghe: A question from Megan — when you set goals, what are they specifically? Per hour or per day?

Ben Wright: I look at it on a monthly basis, because there's so much variety in what we do. Some days are heavy call days with a clear objective, a list, and something to sell. Other days are more about managing your universe — touching base with club members, setting yourself up for success the next day. Some days, a team member is managing our Redchirp marketing and won't be making phone calls at all. So as long as the monthly average is there, that's how I look at the team. It also lets them structure their own days, which I think matters.

Cathy Huyghe: Let's move to tools and resources. I think this will be a popular section — we've already got a bunch of questions. Jenn, let's start with you and WISE.

Jenn Warrington: Sure. We've got some great upcoming classes — and for people on this call, there's a promo code: Enolytics15 for 15% off.

We have a new class called Email Marketing, developed with email experts, covering how to be strategic with email and how it layers with text messaging and outbound phone. We also have an Outbound Phone Sales Management class coming up — great if you're thinking about building a team and want to think through the finances and compensation. For the people you want to get comfortable actually making calls, 116: Outbound Phone is excellent. And 117: DTC Text Messaging — we partner with Redchirp on that one and cover best practices for text-based sales outreach.

We also do mystery shopping for outbound phone, text, and email — not just tasting room. It's hard to know what's really happening from the inside, so having unbiased third-party feedback can be very helpful.

Cathy Huyghe: Mystery shopping for outbound sales — that's super cool.

Cathy Huyghe: A couple of questions came in about tools beyond phone calls — Redchirp, email, etc. Ben and Robert, can you talk about those?

Ben Wright: Redchirp has been a fantastic tool. We use it for marketing campaigns — three or four times a month — but also conversationally. All of my team members have a Redchirp number. We've had great success with team members who might not be as comfortable on the phone just texting customers to check in — "How was your trip to Italy? How was your son's wedding?" And the response is, "It was great — send me a case." Even without a formal structure, a quick personal text to someone who might never answer the phone or is unsubscribed from email can spark a real relationship.

We also use Klaviyo for email marketing.

And I want to give a shout-out to Enolytics, because we run lists all the time. For example, Arizona looks like it's going to be cooler at the end of March, so we pulled a list of customers with high affluence levels in Arizona to target before it gets too hot for the summer. Super easy to do using Enolytics.

Something Chris pointed out is that we use Enolytics to get our salespeople set up before they even arrive at work — so they walk in, hit the ground running, and spend their time actually selling.

Cathy Huyghe: And Ben, you have a calendar with all your marketing campaigns mapped out so your team can plan their outbound activity around what's being promoted company-wide.

Ben Wright: Exactly. That way they can schedule their day around the featured wine or upcoming event.

Jenn Warrington: I just want to plug the RFM tool in Enolytics — that's where we love spending our time. The segmenting and micro-segmenting is really powerful.

Cathy Huyghe: Robert, over to you — and a question from the audience: how do you navigate call blockers and voicemail to stay productive? Do you use auto-dialer technology or analytics to prioritize calling, including by time zone?

Robert Breedlove: We don't use an auto-dialer or predictive dialer — I think that's actually more likely to get you flagged by spam blockers. As long as you're respecting opt-outs and do-not-call requests, we haven't had issues. It's just a matter of continuing to call until you get through, or moving on to the next one.

Our tool stack is similar to Ben's — we use Enolytics and Redchirp, and we're in the process of migrating from Mailchimp to Klaviyo.

I also want to introduce something we built: when our team migrated to Commerce 7, we lost a tool we'd been using in WineDirect for outbound calling campaigns. So a colleague and I built a replacement — it's called Ambassador, and it's now available in the Commerce 7 App Store.

The manager dashboard gives you a quick glance at team performance — activity, trends, results by rep or campaign. The rep view lets you set up a queue, filter your list by time zone, and prioritize follow-up contacts. For each customer, the rep gets a high-level overview: club membership status, most recent order, most recent non-club purchase, and a top-10 list of wines purchased by quantity. All the key information in one place, without digging through multiple screens.

After a call, reps enter structured notes — not free-form — so the data is clean and reportable. Those notes also push back to the customer's account in Commerce 7, so you maintain the full trail.

Cathy Huyghe: I just want to reiterate — Ambassador was organically built from within the industry, based on real experience with WineDirect and now Alpha Omega. We're really glad to be able to introduce it to this audience.

Cathy Huyghe: How does Enolytics interact with Ambassador?

Cathy Huyghe: Both companies are committed to building an API connection. The data will, at one point, flow into Enolytics so you can analyze it. We think it's a fantastic tool — if you have a solid outbound sales team, absolutely request a demo.

Cathy Huyghe: A question from Savannah: how do you decide between sending a bulk message in Redchirp versus an individual one?

Ben Wright: When we first started with Redchirp, we were sending every message to everyone — and it caused a lot of opt-outs. Once someone opts out, it's very hard to get them back. Now we micro-segment carefully. We send last calls and new releases as large bulk messages, but only to previous buyers or people in a specific area for events. If it's just checking in between shipments — a personal "how are you doing?" — then it's a one-to-one text from the assigned sales associate. Keep it authentic, and you'll keep your list healthy.

Cathy Huyghe: We have a short video that shows how Enolytics tools are specifically geared for outbound sales. Chris is going to share his screen — it's about five minutes — and then we'll come back for final thoughts and our special offer. Don't go anywhere.

(video narration): Enolytics has a module built specifically for outbound sales. We call it Sell More Now. It's organized into several pages, each with a specific purpose.

Let's look at Pitch These Wines. If you have dedicated outbound sales staff, you can filter by customer tags — called "contact types" in Enolytics. Filter to your assigned customers, and the list narrows to just your accounts.

Here we're suggesting you pitch the 2024 Silver Springs Pinot Noir to Dalton. He already owns the 2021, 2022, and 2023 vintages — a very good signal. Click the Take Action button to open the Communications window. From here, you can do research on the customer first:

Click AI Summary and Enolytics pulls everything together into a readable summary in about 10 seconds. Worth it.

After the call, click Log Communication — choose your method (outbound call), select yourself as the sales associate, tag it as a sales pitch, set the date, add a subject, write your notes, flag whether it resulted in a sale, and drop in the order number. Submit — and everything is saved to Enolytics for reporting and analysis. If your CRM supports it (like Commerce 7), it also saves as a contact note automatically.

You can also work the list in bulk. Select multiple contacts, click Send to External System, and push the list to Redchirp as an Ad Hoc (bulk) message. Choose your message, name the bookmark, set your spam filter to one-time only, and confirm. Status updates appear at the top as Enolytics processes and sends.

One more thing worth calling out: in Ready to Buy Customers, you'll find Predicted Website Buyers and Predicted Tasting Room Visitors. These are great lists. Predicted Website Buyers shows customers Enolytics expects to purchase on your website in the next 30 days. Predicted Tasting Room Visitors does the same for in-person traffic — so you can get ahead of who's likely to walk through the door.

That's a quick look at how Enolytics helps you sell more wine.

Cathy Huyghe: Any final thoughts before we get to our special offer?

Ben Wright: The Sell More Now module — my team has really loved it. I always talk about researching the customer before a call, and this makes it easy. For add-on sales, if you're pitching the last call of a Merlot and you see the customer also likes Sauvignon Blanc, at the end of the call you can say, "Hey, the weather's getting warmer — let me throw a couple of Sauvignon Blancs in there." Instead of just asking, "Would you like anything else?" you're recommending something specific they've enjoyed. The AI Summary in particular has gotten everyone really excited.

Jenn Warrington: I love that there's technology to help us. Talk to any winery person and they'll tell you they're wearing multiple hats — so having technology that helps you sell smarter, not harder, is amazing. It drives me crazy when I go into a tasting room and they ask if I want "anything" to take home. Don't sell me anything — sell me what I specifically said I liked. That's what Enolytics enables. And there are probably more features in the technology you already have than you're actually using.

Robert Breedlove: In a sales channel that's not always easy — outbound especially — having as much data and ammunition at your fingertips when you make those calls is going to make your team more successful. I think it's great that new tools keep coming out that are genuinely responsive to what the industry needs.

Cathy Huyghe: One final question — what other apps does Enolytics have APIs with, beyond Redchirp and Commerce 7?

Cathy Huyghe: Klaviyo, Mailchimp, Toast — and all the major DTC systems: Offset, Corksy, and others.