My first ride-with was when I was 21 years old. It was June (I had just graduated from college the previous month) and I was working with a distributor rep in Eastern Washington. Within 15 minutes of getting into the car, the rep broke down in tears and told me that she was going through a horrible divorce and bankruptcy filing because her ex turned out to be a con-man who was addicted to crack and had re-mortgaged all of their possessions to pay for his addiction. Unfortunately all of their possessions happened to be in her name so she was the one liable for all the debt. She had been thisclose to purchasing her dream house so that she could turn it into a bed and breakfast, and just like that, the dream had gone up in smoke. All day we visited restaurants that were basically knock-off Olive Gardens, or the occasional gas station with a wine license, and most stops, she would have to leave in the middle of the presentation because she was in tears. I was horrified and wondered silently what my dad would say if he knew that this was my new career.
My next ride-with hadn’t gone much better. This time, I met with a sales rep in a major metropolitan city, and she was over an hour late. She showed up disheveled and hung-over, clearly still wearing the previous night’s club dress, and as soon as we got in the car (littered with gum wrappers, diet pill bottles and cologne samples) she told me we had to go back to her place because she’d just returned from a one-night-stand and she needed to feed her cats. I was bewildered and didn’t know what to do. We drove to her apartment and she insisted I come in; it was a damp, dark basement apartment that smelled like stripper perfume and cat pee. She disappeared into the bathroom for almost an hour (after feeding her cats a half eaten can of tuna), and I just stood there feeling like I wanted to cry. We finally made it out of the apartment and headed to lunch, where she proceeded to tell me her “man troubles” and told me we didn’t need to visit any accounts because she’d “sell the sh*t out of “ my wine anyway. She insisted we walk over to the makeup counter at a nearby department store so she could do a makeover on me (in her “former life”, she was a makeup salesgirl), and somehow I ended the day having spent $40 on makeup I never used again, and visited no accounts.
Luckily after nearly 10 years, the ride-withs have gotten much better, but I did have quite a string of really bad experiences when I first started, and I look back now and wonder how I stuck with it.
So how did I even get into it in the first place?

How I look on ride-withs...
When I graduated from college, I had no clue what I wanted to do with my life. I double-majored in History and Visual Culture Studies (aka Art History) at a small liberal arts college in Walla Walla, and many of my fellow majors were either going directly into law school or were getting ready to begin the graduate school application process. I met with my advisers and they firmly suggested that I take a few years of work in the “real world” before considering graduate school; one of my advisers jokingly told me that I’d be better off going to night classes to learn web-design to start up porn websites because he had some former students who’d done it and were now multi-millionaires (he knew because they still kept in touch, and they had told him all about the endless prospects in the internet world of milk-and-honey). Obviously that was out of the question. I also couldn’t stomach the thought of law school and the expense (and lifestyle upon graduating). Somehow the wine world seemed way more appealing…
During college, I worked two jobs: one at a local wine bar/wine shop during the week, and on the weekends, I worked at a local tasting room. Somehow I managed to get a meeting with the national salesperson for that winery and was offered a job doing regional sales, starting as soon as I graduated. The problem was that I had zero training, zero knowledge of the wine business outside tasting room sales, and next-to-zero knowledge of wine outside Walla Walla.
I had a few cursory meetings with my new boss (who frankly was nearly as inexperienced as I was when it came to working on the supplier side), but she did tell me that I needed to start doing these things called “ride-withs.” These “ride-withs” were basically an entire day, where I, the winery rep, would ride along with a distributor sales rep and visit between 6-10 of their accounts, and at each stop, pour wine and make a sales presentation for the wine buyer. The function of the ride with was multi-purpose:
1) Sell wine—the hope would be that at each stop, the buyer would enjoy the wines enough to put them on his wine list or shelf, and maybe even get a wine by the glass or on display somewhere
2) Educate the sales rep—after 6-10 repetitions of the winery story and information about the wines, the sales rep would (hopefully) remember those details and be able to share them again when presenting my wines to other accounts in my absence
3) Build a relationship with the sales rep and the accounts—spending the day in someone’s car provides a great opportunity to get to know someone. Additionally they introduce you to their buyers, which can hopefully lead to direct communication between you, the supplier, and the buyer
4) Show the distributor that you support them in their efforts and that you are committed to a successful and fruitful sales relationship
Some things I quickly learned are very important on a ride with:
1) Have a sell sheet e.g. a list of the wines you are showing, along with prices and pertinent information on the winery/wines.
2) You should probably know about the wines you are selling. This seems like a no brainer but I’ve heard that a lot of supplier reps have no clue about the most basic details of their wine (vineyard locations, oak regime, alcohol, cases produced, etc.)
3) Keep a record of whom you visited and what you showed. Write down what they liked and get their card so you can follow up with a thank you, and judge your success against depletions.
4) Be flexible. Remember that distributor reps have a lot to juggle and sometimes have 3 ride-withs a week during busy seasons. Sometimes accounts cancel and sometimes things go wrong; those things are often out of the control of the distributor rep. Besides “moving boxes” you are there to educate and build relationships as a winery ambassador.
The bottom line: ride-withs are an essential tool to build sales for your winery. Although not all of them go as well as you’d hope, you will have some great stories to tell so when you look back on those bad days, you can remember them with a laugh.