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Game-Changing Initiative: How A Top Leader Brought Penny to Traveling Vineyard

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Penny Fitzgerald is an Emerald Director at Traveling Vineyard. A wine guide for over 15 years, Penny loves sharing the joy of drinking a good bottle of wine while learning something new. 

When Penny Fitzgerald discovered Penny, she knew it was a game-changer for direct sales. Learn how Penny brought Penny to Traveling Vineyard.

“It was over Thanksgiving weekend, and once again I was looking for a personal solution to track my Wine Guide leads’ progress. I had been researching to find a tool that could help my team but everything was too corporate focused or for B2B. I searched the app store on my phone and found Penny. At first I thought it was too good to be true! But, pretty quickly I realized this was going to be the game-changer my team and the whole of Traveling Vineyard needed.”
Penny Fitzgerald, Traveling Vineyard

Penny’s Journey to Penny

When I first downloaded Penny I wanted to know exactly how to use it to grow my business, I chatted with Vic from Penny’s Customer Success team and we asked each other so many questions so I could learn about Penny and she could understand exactly what I needed. She then recommended I see a full demo of Penny platform and learn about all the features available in Penny Thrive and beyond.

It was at this point that I realized how Penny could help me proactively support my team instead of reactively. And that would be a complete game-changer not just for me but for everyone at Traveling Vineyard.

Traveling Vineyard

What Penny saw Penny could do for her Team

“I felt so strongly about Penny being a win for my team and Traveling Vineyard that I added it to my annual personal goals because I saw how it would bring such a lift to the company and the way we run our businesses.”
Penny Fitzgerald, Traveling Vineyard


Personal connections are the most important part of direct sales. Penny helps you navigate all your different relationships without being overwhelmed. For Wine Guides on my team, Penny simply tells them what to do and when to do it to see the best results. The daily to-do list reminds you to reconnect with someone who’s placed an order, follow-up with someone who’s booked an event, it even tells you the weather in that person’s location!

Connecting customers' profile cards to their social media and allowing a space for notes, it all helps you quickly customize your message to a customer and pick up where you left off. The saved scripts and content preloaded into the app that we can add to and share with our team — saves so much time as well. All of it, it’s just amazing. It truly is like having a personal assistant tracking everything that is happening in your business. And for leaders, it helps you keep track of your team as well.

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Bringing Penny to Traveling Vineyard 

I’d been looking for a solution for so long I almost thought Penny was too good to be true. I sent the details to some of my elite leader friends in December. They checked it out and immediately loved it. They saw as well how big this could be for the company.

“I knew we still needed more firepower before we went to our World Headquarters so we got some of our team members to try it out. They all immediately fell in love with Penny. Like us, they saw how even more powerful Penny would become once connected to our back office.”
Penny Fitzgerald, Traveling Vineyard

Our company is really open to ideas from the field and so at our monthly elite leader call with corporate, I added Penny to the agenda. My elite leader friends were able to throw their weight behind it and we had the proof and quotes from our team about how well Penny was working for us already.

Mark from Penny’s sales team was really helpful and did a demo of Penny for anyone who was interested and several people from corporate and IT joined to learn more.” 

Traveling Vineyard Screenshot

From Early Adopters to Company-Wide Solution 

“Now that Traveling Vineyard has Penny, I’m working with other leaders to help get more people using Penny. At our annual company convention, Elizabeth Allen and I are presenting Penny. Telling everyone first hand why they should use it but also we want to show them how we’re using it to run our businesses.

At the moment Penny is an Opt-In system, but we’re putting a proposal together to make Penny an Opt-Out system so that everyone starts with Penny so they’re set up from day 1. There’s already so much going on when you first start a business, I know Penny will help cut out the noise and set new wine guides up for success.

To wave the Penny flag, we’re also continuously posting in our team groups, letting people know about different Penny features, and our users’ success with Penny already.

Elizabeth & Penny Harvest Training 2018 Zoomed

Leaders: Proactive VS Reactive Leadership

“As we all know, being a leader in direct sales you don’t actually know whether your team is working hard and seeing success until you get paid. In direct sales, what you do today is going to benefit you in 6 weeks. There's no mechanism to reward people when they are actually putting in the work. You don’t know how many phone calls they're doing or how many touches they’re making. But with Penny, you can.

The best thing about Penny is that I can see my team’s activity and then reward my Wine Guides immediately for their hard work. I can also follow up with someone if I see that they haven’t been as active as usual and proactively see if they need support. Or if they’re putting in a ton of effort but not seeing the sales and bookings they want to achieve.” 

Penny Beginners

Wine Tasting Pool

“I wish Penny was available 15 years ago when I was starting out. I think for a new Wine Guide if they get started with Penny they are going to be successful right away as it creates good habits from day one. Putting one foot in front of the other, making you successful, telling you exactly what to do and when to do it… it’s priceless.”

Penny Fitzgerald, Traveling Vineyard

Penny for Established Leaders

For some Wine Guides with a large team it is more lift to set up Penny in the first place if you’re using Essential or Thrive and it’s not connected to your back office yet, but once it’s set up then Penny makes everything so much quicker and easier. When Penny is connected to your back office life becomes a lot easier!

Trusting Penny was the hardest part for me, we’re all so used to having to dig into our customers' details, cross-reference notebooks and spreadsheets and our back office, double check time zones etc. It’s crazy! But now Penny just does it for me! I love that I don’t have to remember to follow-up because Penny never forgets. 

For other leaders looking at Penny I say, take the leap, give up the control, trust Penny and your business and life will massively improve.

I have lots more plans for using Penny, organizing ‘Booking Blitzes’ so I can reward my team and shout them out while we’re all working together and I can see the tasks they're completing! I’m also excited for when we can run our wine events through Penny itself — Penny is always rolling out new updates to support direct sellers.” 

Travelling Vineyard Help

Penny’s Favorite Feature

“I love the ‘Thank you’ tasks. When someone orders and then the Daily reminds you to send a Thank you to the customer — that has been instrumental in driving new business from existing customers. They just experienced a tasting, made a purchase and it keeps the momentum going. Helping to get more bookings and more orders and spreading the love. It’s such a simple message but so often we’re looking ahead at the next customer and the next order that we forget. Having a built in ‘Thank you’ task reminder has opened up even more business for me as I gain more repeat customers.

Love the culture at Penny as well. Everyone is so positive and quick with awesome Customer Service every single time.

Love What You Do

What was your Experience with Penny over other Tools?

Penny has everything and if it doesn’t the team is so amazing at listening to what you need and adding it into the roadmap so next thing you know, the feature is there! And along the way, the Customer Success team is incredible, so quick and friendly to help sort out any issues.

For direct sellers, there can be some reluctance to look into new digital tools because we’ve had tools in the past that simply don’t work. Or, the tools have all these workarounds to actually do what we need them to do. Nothing can compare to Penny and the best thing is that it just keeps on getting better.” 

Do you need help managing your business, your customers, your team, your social engagement?

Discover Penny Today >

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