THE REORDER 05/21/18

The Dark Side Part I – The Wine Sales Interview

Are you coming to the dark side*?

With the proliferation of import/distribution companies in NYC, there are more sales positions and opportunities available than ever, but little clarity on what it takes to put yourself in the best position for success as a salesperson at a good company.

I am hoping you will let me throw you a little inside baseball. Let me ‘leak’ some advice…

Below are some key points to consider when you are interviewing for a sales position in the city. As obvious as they may seem, it is exceedingly rare that anyone thinks this through enough to do them.

And just in case it bears repeating: There are many roads to Rome. What is below is not a one size fits all perspective. The market you are in, the standard practices of the distribution companies and the character and scope of the portfolio you sell will impact the below.

#1 Know the props and players

Ideally, you should walk into an interview knowing the company portfolio well. The history, who is behind it, where it is going. Take the reins and do more than a little research. Who are the props and players and who has which producer? The better you have a handle on the market you are interviewing in will directly impact the choice (and level) of companies you interview with. Essentially, the more you know the import/distribution scene, the higher the echelon of company you can go, and in turn, the better choice in companies to work for you will have. No viable company sleeps on someone that really knows a market.

#1a – curveball question: Why didn’t you buy from us?

If you are a buyer (or were) and never really bought from** the company you are interviewing with, you should be ready to answer why, and you better be convincing if you want the job. Also, have you considered that who you are buying from currently could be your most connected contact for a new job?

#2  The playbook no one thinks of…

Inventory is one of the most misunderstood and least talked about elements of a company in sales positions across the city, and yet, it is a vital ingredient to success.

Think of it like this: the inventory, open availability and producers will be your wine list. If you only have a few cases to sell of that sexy Beaujolais customers ask you for – you need to know that you have other options to take them to when that is gone. You need a spectrum of choice in your figurative bag. If not, you are going to run into problems once you really start selling wine (from an availability/volume point of view) – and these problems can be crippling and create a concrete ceiling. I speak from experience and this dynamic isn’t pretty.

Once talks get real (real enough to feel comfortable), ask to see the full inventory with associated availabilities (limited availability wines and their allocations, wines that sell out in a day, etc.) over several months. Ask what the seasonal flow is like. Do they DI offer their Rosé, for instance, or do they stock Rosé?

I guarantee you that most companies will be shocked that you are asking about inventory because most potential salespeople never think of this. Bottom line: You need to know what the inventory looks like and how it functions to make waves. You must have inventory/supply to sell to succeed.
The companies that are serious about hiring you and aren’t transparent about inventory are giving you a hint about what it will be like to work for them. If there is some concern on their side about transparency with you then tell them that you understand that inventory + accounts + passion + thoughtful work + connection = sales.

If you are missing the inventory piece, it is extremely difficult to find lasting success. And don’t forget that the more you sell, the better for the company.

#2a The small ball game

Imagine that portfolio that everyone says is “on fire” with the owner/partner who is also a salesperson. There is a very good reason that the owner is selling. I bet you that there isn’t a good spectrum of wine to sell with inventory behind it. There are exceptions, of course, but this is generally the rule. And this is not to take away from the strength of these types of portfolios, some of my favorites in the city are these portfolio models and I would bet on a few of them, but that doesn’t mean it would be great for you to work for them today.

#3 Culture Club

I would argue that the culture of a company has just as much to do with the quality of the portfolio as the wines in it. It has a massive impact. But, it is difficult to interpret and understand the culture of a company from the outside.  I always advise talking to reps in the market about what it is like to work at the company, both current and former. An importer/distributor with a “good” portfolio may come with owners/managers that are not good to work with. No one says when they are hiring: look, we are shitty to work with, but the wines in our portfolio are great.
Insider tip: if they have a portfolio of note, but a regular turnover in prime sales positions, I would be very aware of what that says about the company culture before interviewing — and if the vibe is right during the interview, I might even ask why they have had the turnover.

It is easy to be hypnotized by the wines in a portfolio and not understand that the culture within the company impacts how it will be to work with those wines.

#4 And…the account goes to…

Always ask what type of accounts will be available to you.

No matter what your level of experience, importer/distributors are generally cagey about which accounts are available, and every once and a while for understandable reasons. Figure out which type of accounts you will have access to as a rep and how the company decides who gets assigned to which account.

And if they say “we have house accounts and dead accounts for you with a lot of potential,” I would ask to see the list. I might even request ahead of time that they note all accounts that have trouble paying or have had recent buyer turnover. Generally, dead accounts are dead for a reason. Pulling blood from a run of dead account stones is a really hard game.

Now, the hard part that is basically unheard of:

#4a The Bait and Switch

Once it has been decided and you are getting an offer that includes accounts, mention casually that you have heard that companies switch runs on new sales reps and ask for some sort of assurance. 

Why? I have seen the bait and switch NUMEROUS times at high-level companies. As in – here is your run, and when you show up on the first day it is different than what was promised. If they are committing to you, they should be open to it. But also keep in mind that you will have to feel out this moment, and trust in the outcome – just make sure you feel comfortable with what you are walking into.

You need to know what the inventory looks like and how it functions to really make waves.

#5 Understanding commission and expectations

The way reps earn money varies wildly. Some are on a draw, some are 100 percent commission (in which you need to know the average commission), some are on salary with bonus opportunities, and there are variants of all of the above. If you have the inventory and know the accounts you will get – you must have a handle on the commission or payment structure you to project how you can support yourself.

Most companies do give 6-12+ months of salary as support when someone starts. This is “fairly” standard, but can vary as wildly as the pay structures.

Question is: what happens when you are off the support? Can you handle it? Look ahead and be realistic.

The Final Decision

If you have a good handle on the people you are working for, the portfolio and inventory available, the accounts you will have, and the way you will support yourself, you should be able to make an exceptionally good decision on whether to take the job, run quickly away and/or keep looking.

Once you have the job, your world changes quickly…This is where the tough part starts. Getting things rolling as a sales rep is a little more complex.

Part 2. Coming soon.

*the dark side is a common term used to describe beverage sales

**there seems to be some general confusion about what “buying from someone” means. It means you bought regularly, you gave a BTG or two, and always kept them in the game. Why would you want to work for a company that you put in the low, non-existent slot in your rotation as a buyer?

THE REORDER 04/16/18

Wine Sales – A top 5 don’t do list

Wine sales can be tricky. Unlike other sales jobs, there are few “constants” and the sales cycle is shorter and more unpredictable. But I am seeing a lot of mistakes repeatedly made on the street that can be easily remedied. Below are the classic top five mistakes and some thoughts on how to avoid them.

I hope this helps.

#1. Fetishizing the appointment

It is romantic to think that sitting and tasting wine with someone will solve all sales problems and make everyone understand, but I can tell you with confidence that the moment you start fetishizing the “appointment,” you are lost. It is over. Finito.

You must find another way. The answer is in this question: Why would they ask YOU to sit/taste and not the other way around?

#2. Account Hunting on Eater

Trying to find new accounts? Eater should never be your primary source. Do pay attention to it, because it CAN give you a heads up, but keep in mind that everyone else sees it – and therein lies the problem.

Best way to find accounts in NYC? Take a walk. I know, it is a lot less sexy and requires much more time, but you will find much more gold. Many worthwhile accounts in the city never appear on a Heatmap. 

#3. Preparation and the Bag full of “everything”

I used to sit at a bar in midtown waiting to taste behind a line of reps and watch them open twelve bottles of wine for a buyer that was rarely going to buy one case from them. Contrastingly, I would roll in with less than 4 bottles and the buyer would take a few cases. There was no genius in this, I had done my work before I got there. I knew what the gent liked and what in my portfolio had a chance.

Never open bottles for a closed mind – and do whatever work you can ahead of time to know what you have that is actually worth showing. Also, (and most importantly) avoid the trap of trying to have a bag full of wine that has something perfect for everyone. It can really lock you up. This bag of wine doesn’t exist, and you will always be missing something. Don’t worry – this is a good thing.

Many worthwhile accounts in the city never appear on a Heatmap.

#4. ‘Over Talking’ the Wines

Don’t over talk the wines. Want to have connective conversations with some of the best wine professionals in the world that buy wine in NYC? Stop ‘over explaining’ the technical, mundane, google-able aspects of the wine and get to what is true about it.  If you actually know something deeper, artfully share it.

And while you are at it, ask a question and just listen. Watch how someone tastes. Learn from them. Then think about how you present wine to them.

#5. It ain’t surgery, it’s the wine biz

In 2007, a superstar veteran salesperson said something to me that changed my career. He told me that I shouldn’t take this job too seriously. Even though I was struggling at the time just to get by, he was right. I smelled of fear, and no one wants to work with that. Faint desperation is not a good look.

Stay as light as you can with the job of selling wine. If you have to have that sale, you need to re-evaluate what you are doing so it isn’t that serious.

THE REORDER 03/05/18

Reading the Tea Leaves – Classic Wine Buyer responses

Let me read the tea leaves of some classic buyer responses below. All of these interactions can be overcome but can take time and serious investment. It is always going to be nuanced from buyer to buyer, but if you see the meaning, it gets easier.

So, below are translations of some common buyer sayings. Think about this: maybe that the buyer may just not be into you and you need to find another? What you have to offer may not be for her (or him)…don’t be afraid to move on.


I don’t know your book

I don’t want to know your book, or more likely, you need to entice me. Go for the top producer in your book that you can think of and watch the reaction.

I work a lot with consignment

They like historical prestige labels and will like to play with traditional over new finds. They also tend to dislike most import/distribution operations. Look for the producer connection.

I like recognizability

I like big, established brands and my list could have been written in the 90’s. Have you had Staglin? Super tough one to win with unless you have a book filled with big brands.

I can’t take any more distributors on right now

I have my chosen people. This one is VERY HARD to get past. Choose to spend your time wisely.

Email me...


I need to think about this and I want to see your email game. Email them like you know what a buyer wants/needs but without arrogance.

I don’t do appointments

Every buyer does some form of appointment…Every one of them. You just need to figure out what that means for that buyer and be there. Sometimes the email offer is more viable.

What do you have that is on closeout

We look for pricing deals, not quality deals. Question for you: Do you want to play ball with this type of customer?

Most of the time buyers have “tells,” and it is your job to be a good listener and an even better observer.

THE REORDER 02/19/18

White Knuckling the Problems

White knuckling the problems don’t ever work as a sales rep. I have tried and I can tell you this with certainty: it makes it much worse. Below are a few problems that have stood the test of time. I have seen them over and over again, and have made endless mistakes dealing with them by force.

The Classic Problems

Inventory will never be correct. It is the Rubik’s cube that will never be completed.

The market will fluctuate. Up. Down. Up. Down. I have been through both. There is always something to see more clearly, and no matter what anyone says, neither up or down markets are easy.

That buyer you work so well with probably won’t be there forever.
The moment you think it will align and there will be an eternal thunderclap of business, they will move on. Enjoy your time.

They don’t respond to emails, so you have to find another way.

The office isn’t against you. A “back of house/front of house conflict dynamic” will be pushed forward by someone. Ignore it. Whoever wants to instigate the classic “us against them” within a company is a mediocre professional at best and will pull you away from artisan sales.

The blame game trap. There will be pressure to scapegoat all the time. Ignore this, too.

Whoever wants to instigate the classic "us against them" within a beverage company is a mediocre professional at best and will pull you away from artisan sales.


What are you missing? What can you see that others can’t via the work you do and the portfolio you sell?

What do you say to yourself every day that can move you forward without just white knuckling it all?

Selling wine and spirits thoughtfully is ridiculously difficult to execute well. Don’t make it harder.

THE REORDER 02/05/18

Always. Be. Opening.

Orders are rolling in and people want to see you. You have alive accounts, enough wine to sell, and new wines coming into launch. Your run is busy. You feel confident and safe. Your accounts are a train gaining momentum…until…they aren’t.

When your group of accounts seems the most solid, like a battalion of ships that could never sink, do this as a practice:


Not just the referrals, not just the ones that roll your way by chance, I mean actively seek out new accounts.

The Lie

The stable run of accounts only exists in the land where DRC is always poured from magnum and restaurants are open forever…

Even though those around you may talk about your accounts like they are a sure thing, they actually never are. It takes a heroic amount of work to thoughtfully run a group of accounts successfully and consistently as a rep. Don’t ever sit back and think you have a gimme because it doesn’t actually exist.

Once your accounts reach a certain density and size, change is not only probable, it is inevitable.  Buyers will move, restaurants will fail.  What once was an account with a few glass pours will go away because of availability, or that new buyer will think the wines on the list that were working well work a little ‘too well’.
If you choose not to continually and actively develop your account base, you will reach a point where you will start to lose. This is the aging run phenomenon. The old-school salespeople will talk of days gone by when this wasn’t the case..but the market is much faster now.  You have to be active.

Consistently opening new or underserved accounts is the only way to mitigate the volatility of the NYC market.

New Blood

Like a wine list, a run of accounts has to be managed and developed. Keeping a fresh, diversified group coming up into your run of accounts is a necessity.

The opposite is also true: having too many accounts and running around paranoid opening new ones to replace others is an even more horrible road to take… the chicken with the head cut off approach isn’t pretty at all.  The total accounts have to be viewed through the lens of the portfolio–there is no one size fits all approach. But go too far with opening accounts and you will know.  This is why you have to not only open but develop.

When you start to relax into your sales run, think this:

Always. Be. Opening.

THE REORDER 01/15/18

The Hard Road – An Honesty Policy 

Early on selling wine I realized I had to make a choice: be honest and sell less in the near term, or be deceitful and sell more. This was not a difficult choice for me because even the smallest half truth causes me sleepless nights. So, I chose to lose early with an honesty policy and hopefully win later with trust, even though supporting myself was in question at the time.

I have never regretted that decision and would do it all over again. Even though I know some salespeople in this market routinely hide the ball and “play” with their customers for sales, I watched them and learned what not to do.

Some classic maneuvers: hiding a price, then making it look like you made the deal, lying about farming practices, or lessening availability to make the wine seem more valuable…It is a big list of half-truths and it goes on and on. The honest salesperson doesn’t play in this neighborhood.

I definitely could have taken multiple shortcuts and made the numbers look unbelievably sexy. There were opportunities to goose the whole market that I passed on, and I am certain other salespeople would say it was insane to not take them. This may be a harder road, but ultimately,  it was a foundational choice and I am staying put. Anytime I get the chance to give advice, I always mention this choice first because it defines a sales career.

Most buyers are accustomed to schnookery, or blatant sales tactics, that rely on jazz hands and a big finish, not the simple subtlety of an honest salesperson.

The Conflicts

There are conflicts that arise after you make the decision to be honest with your customers. First one: every buyer says they want honesty but very rarely are they prepared for it. It isn’t their fault, actually, it is ours – the wine salespeople of America.
Most buyers are accustomed to schnookery*, or artful (many times deceitful…) sales tactics, that rely on jazz hands and a big finish, not the simple subtlety of an honest salesperson. A buyer of wine will be surprised, and possibly put off by honesty, at first. Don’t be deterred, it is natural to react this way. Stay the course.

The second one is that the delivery of honesty needs to harmonious with you and your style of communication, not used as a blunt instrument. You know what I mean. Honesty can be dropped like an anvil. I am not saying to never do this, but approach with extreme caution. Everyone is the author of their own experience, etc., but the way you communicate impacts the tone of the dialogue.

Stay true, honest, and genuine, and this road will lead you to great people and trusting relationships. Nothing but good comes from this dynamic.

*Schnook is defined as a dunce. In recent years, it has become synonymous with a wine salesperson due to poignant and sarcastic writing by the late Joe Dressner.


Five Questions with Caitlin Doonan, Assistant Director of F + B at the William Vale Hotel

Caitlin Doonan currently works for NoHo Hospitality as the Assistant Director of Food and Beverage at The William Vale Hotel, working with 7 venues including Westlight, Leuca, and Mister Dips. Before making the jump across the East River, She was on the opening team and spent four years at Ken Oringer and Jamie Bissonnette’s Toro NYC as the Beverage Director and GM. Caitlin has previously worked for David Chang at Momofuku (Ma Peche), and Jean-Georges Vongerichten (Market, Spice Market), and others.

Five Questions with Caitlin Doonan

Which wine (or wines) do you believe in that your colleagues in the industry disagree with you on?

I would imagine there are quite a few! Spanish Bubbles is definitely a category I love more than most of my peers who seem to vastly prefer Champagne. Now, of course, there are many Champagne producers I love and drink regularly, but I have a special place in my heart for the traditional method Sparkling wines from Penedes. When you taste fine examples of Spanish Sparkling, from producers like Recaredo, Gramona, Raventos i Blanc, Castellroig and more, there is a core of ripe fruit, provided by the bright Mediterranean sunshine, that doesn’t exist in most Champagne. To say Spanish Sparkling is good if it tastes more like Champagne is crazy. If you travel to both places, you know this would be very odd, but I hope that one day the excellent Sparkling wines from Spain will be a part of the same conversation regarding excellence, complexity, and quality as their counterparts in France.

Which trend or trends in wine (or spirits) do you wish would go away?

Pretty much everything! The only trend I’m truly supportive of is the drive to educate more – ourselves, our staff, our guests. But perhaps I’m dodging the question. The trend that probably annoys me the most is many wine lists starting to look the same. There’s too much “wine list as ego boost.” If a wine list says more about the Wine Director than anything else, it might be full of allocated gems, but it’s probably pretty boring.
And it must be said, the trend of many powerful men in the Restaurant industry turning out to be disgusting predators – yea, I’m ALL SET with that. Achieving excellence in this industry requires passion, vulnerability, dedication, and focus on the highest of levels – this is business and it’s art – the last thing anyone needs is their boss making their workplace toxic. People who need to make others feel small so they can feel big have no place in this industry. I am infuriated that so many people have had to put up with this kind of abuse to pursue something they love. I applaud the victims who’ve spoken out – their courage should be revered by all of us, and I find the response by those who enabled this behavior for decades to be craven, weak and lacking soul. We have so much work to do.

If you could ask one question of other wine directors in the city, what would it be?

How do you approach education? I view this part of my job as the most important, but it sure is a challenge finding the time! I’m always interested in how my peers approach educating their staffs, and themselves.

What do you see as the biggest challenge for beverage directors in the next five years?

One of the things I think about every day is how to make sure my team feels valued. The great thing about millennials is that they feel they have something to say, and they want to say it loudly. Point of view and a drive to share it are marks of an exciting generation! But they also have high expectations of their leaders. I try to meet those, and I’m sure many days I fall short, but it’s on my mind every day. Definitely a challenge. I also think one thing we’ll continue to see as the minimum wages rise (a great thing – living in NYC on $11/hr is a joke) is the consolidation of positions. Seeing the value of a beverage director to a business requires foresight and a bit of creativity – it’s not always as obvious as the value of a General Manager. I hope that will change. I hope the great beverage directors become business owners!

You wrote an important wine list for Spanish wine at Toro NYC with an impressive array of Sherry, Village, and Bodega Rioja, etc. –
What is the biggest barrier for Spanish wine today? And, what has the most promise?

Oof! What a question! First, I have to say that Toro was the best playground for my 4 years there. The wine list evolved considerably over time, and my staff were stars in their dedication to spreading the word about Spanish Wine – they weren’t intimidated by anything – single parcel Garnatxa Peluda from Montsant? Sure! They just got on board. I’m very proud of the successes of that program, big and small, and I recognize that they are 100% shared. Running a Spanish program is like being a Red Sox fan pre-2004. There are small victories along the way, and you love it, but you are championing an underdog. Quite honestly, the biggest barrier for Spanish wine today is $6 Albarino, $8.99 Cava (can we all make a pact to stop buying this?!), and marketing. There is NO better country than Spain in terms of value. For $20, you can buy an exceptional wine. But the US has been flooded with crap from Spain, so people associate Spain with “cheap” wine. The good stuff, even if inexpensive, does not make it out of major markets. My parents live in CT – it’s a train ride away but it might as well be across an ocean for how easy it is to get Spanish wine there. On a “global” wine list, there will be 3 Spanish selections, and one of them is probably the same Rioja that everyone else has on their list. There just aren’t a lot of wine professionals who spend a lot of time with Spain. Even in study guides, Spain gets the same amount of room as one region of France. So this is a multi-layered problem. It’s difficult to know where to begin in tackling it. At Toro, I tried to just get as many different things in peoples glasses as I could, and people were open to it. But I had the luxury(?!) of most people opening the list and not knowing most of it, so needing the guidance anyway! We live in a world driven by the social media “influencer” (call back to trends I hate!) and these excellent, small wines don’t have marketing budgets. Additionally, each region has it’s own marketing machine funded predominantly by the large bodegas so there’s not much incentive to promote the little guy who contributes less (wine, politics, it’s all depressingly the same). So, Spain needs champions!! I’m not sure there’s one region that shows more promise than others. I hope we figure out the Rioja puzzle at some point – a bit of a personal crusade of mine. Rioja should be classified by village, like Burgundy. I know we’re no longer living in a science-respecting country, but there’s plenty of objective evidence to show large terroir variance village to village. But unless some very large Bodegas want to admit they don’t have all the best vineyard sites, nothing will change because they pay the bills. This is getting a bit depressing, so on a positive note, I think the wines from Galicia are getting more good attention. Seaside Albarino from Rias Baixas, indigenous field blends from Monterrei and Ribeiro, and pristine Mencia from Ribera Sacra – it’s exciting to see. I’m hoping that Spain will be an easy entry point for young wine drinkers and wine professionals. It’s tough to go into a shop and buy a bottle of Bordeaux from the 1980s – who can afford that – but 1980s Rioja is much more accessible. Because of the built-in system of holding back wine (Crianza, Reserva, Gran Reserva), even the new releases are older. And many Bodegas have a large stock of older vintages so they’re available on the market. Perhaps that will be a way for people to fall in love with the region and country!

On a "global" wine list, there will be 3 Spanish selections, and one of them is probably the same Rioja that everyone else has on their list. There just aren't a lot of wine professionals who spend a lot of time with Spain.

BONUS Question from Nicole Hakli of Momofuku ssäm bar:

Our profession as sommeliers is more like an apprenticeship and an art that gets passed down each generation. Who mentored you along the way? What made them a great leader? How will you choose a mentee?

I think I view the profession a bit differently. I’m from a family of educators, and learning has always been highly valued. I have learned from a lot of incredible people, but not all Sommeliers. Theresa Paopao took a huge chance on me years ago at Momofuku, and she is still someone I look up to. She made wine fun and accessible and never took herself too seriously even though she was a BOSS!! But, while wine is the medium I love to work in, I’m more an educator and a cheerleader than anything else. I learned everything I know about pairing from working with Chef Paul Carmichael. Ken Oringer and Jamie Bissonnette taught me the importance of professional agility – to be able to adjust and find solutions on the fly. Kyle Eakins and Lianne Raymond (Toro CDC and Events Director during my tenure) taught me the power of tempering my intensity and the importance of connecting to the human part of our staff not just the work part. And perhaps most far afield, my voice teacher at The Boston Conservatory while I pursued my masters, James Javore, taught me that you can only teach if you can listen. I tend towards the impatient. I want to get sh*t done – but stopping to truly listen, with no agenda, is the most important work I do. As for a mentee – I don’t think that’s up to me! I don’t believe that what I am able to teach is meant for one chosen person. I hope my team learns something from me as I do from them each day. Whether someone chooses wine as their lifelong career path, or merely a pitstop, I hope I can make a positive impact on their journey.

Follow Caitlin on Instagram @ccrosbiedoonan

Note: all answers above are posted without any cuts or edits.