Online Sales Strategy

It Ain’t Showbiz.


If I asked most Drift readers what they do for a living, they’d offer up a job title like chief revenue officer, account executive or regional director. If pushed for a more concrete job description, eventually most would say they sell advertising, technology or services to marketers and agencies.

But I don’t think that’s what you do at all. At best, selling describes an outcome, a result of other actions you take every day… at least, if you’re doing it well. It’s taken me a long time and a lot of observation and introspection to get there, but I think I’ve nailed what great sellers do: they engineer experiences. The mediocre ones? They’re the ones who get all caught up in the performance they’re giving, the lines they recite, and the slides they flip through.

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A sales call isn’t a golf shot or a piano sonata. But so many of us prepare and act as if it is. We drill ourselves on our lines, memorize key points, practice the voice-over for the 37 slides we’ll show, test the demo to make sure it purrs like a kitten. We believe that if we only perform well enough and hit all of our high notes, the power of our words will impress and persuade.

Only it doesn’t work that way.

Now, reframe the sales call as a shared experience. You and the customer are both living in that moment together, and now it’s your job to engineer that experience… you’re no longer the funniest guy at the party, but rather the host who’s creating an awesome environment for his guests. What will you do differently?

You’ll attend. As in, the root verb in attention. Ironically, attending is also the same as being present. Get it?

You’ll know something about your guests. There are no strangers. You can always know enough to make the other person feel interesting.

You’ll draw people out and make connections. Use what you know to bring the other person into the experience. This is the opposite of bludgeoning them with your own story.

You’ll have a plan and watch the clock. Great hosts pay attention to time and pace. They know when things are starting to drag, when people start to disconnect.

You’ll rewrite the plan when you need to. If things are petering out and nobody’s connecting, change the plan. It’s your plan; you get to do that.

Sales is not performance art. It’s about creating a fertile space where trust, emotion and opportunity can grow. Too many of us become tone deaf from listening to the sound of our own performances. Let it go. Be interested. Engineer a great shared experience and watch how everything changes.

Including you.

Originally posted in 2014, but still well short of the expiration date.


Web 25: Targeting and Personalization


Late October will mark the 25th anniversary of advertising on the Web. Having been part of the team that ushered in those first primitive digital ads in 1994, I’ll be using this space in the intervening weeks to explore the fulfillment, failure and future of the web’s marketing and social promise. This week, Targeting and Personalization.

As our small team of outlaws were selling the first ads on the web, it would be more than a year till the invention of the first ad server.

Think about that for a minute.

There was no practical way to serve an ad independent of the page it was selected to run on. User targeting was impossible. To us – then – it was enough that a marketer could talk to a customer based on whether she was viewing a page about home improvement or cooking. That you had an opportunity to advertise at just the exact moment when relevant attention was being spent was, at the time, revolutionary.  Of course, that moment couldn’t scale and wouldn’t hold. Change was inevitable… but what kind?

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The deal we struck with consumers (or at least told each other at conferences) was better and more personalized advertising and content experiences in exchange for data. We’ll be watching you, but we’ll make it worth your while.  By even the most charitable estimate, we haven’t lived up to that bargain. We went on a serious bender of infinite supply and cheap data…and the hangover is a bitch.  Seeing no value, consumers have revolted. Politicians of all stripes are engaged. GDPR has led to CCPA. And major marketers are demanding heretofore unseen levels of transparency and purity.

And as a result, just maybe we’re getting back to what made this all special in the first place.

No one is naïve enough to think we’ll go backwards to a world without ad servers. But look at what is happening. First party data is quickly becoming table stakes. Marketers are taking a fresh look at context: they are moving beyond brand safety and looking for brand building environments. There’s been a boom in content marketing and high-production-value video adjacencies. Publishers are rising to the challenge of delivering real personalization and reciprocal value to marketers and consumers.

We’re not going to start hard coding ads onto web pages again. But if we pay attention, we might realize that we’ve found the source code for a healthy web for marketers, publishers and consumers. A little bit of ’94 might still be good for us.


The Holding Pen.


Five years ago in this space I wrote about The Illusion of Inclusion – the already-dysfunctional agency RFP process that gave digital sellers a false sense of progress and scuttled their sales activity before it could do any good.  Five years later the contours of the problem have shifted, but its impact is even worse.

In the scores of sales workshops and interviews I conduct, I still hear about well-intentioned sales teams pitching clients and conceiving ideas only to then get told We’ll be sending out RFPs in a few weeks.  More unfortunate still are the reps and organizations whose sole intent is to get a spot on that ill-fated RFP list.  In the intervening five years – as programmatic buying and consolidation have taken root — the number of winners has gotten shorter and the environment has gotten far less hospitable to non-platform publishers and sales orgs.  And participation in the process has gotten far more costly:  today’s RFP submission may include outside talent, events, technology, design, yield and more.  And all in service of a process in which you may never have had a chance.

Every sales leader wants a team that’s more proactive and strategic – a team that controls its own destiny.  But how to get there?  A sales workshop with Doug Weaver and Upstream Group is easier and more cost-effective than you might imagine.  Reach out to us today to discuss what you want for your team.  The consult is free.

Those whose offerings lean more into programmatic inventory, data and ad tech services may think none of this applies to you.  But it does.  We’re going to be looking at new vendors in Q1 and we’ll including you in that bake-off is just one example of you being effectively told to take a number.  The truth is we are all working harder to get the consideration of buying organizations that are operating short-handed and who don’t necessarily have the full confidence and commitment of their clients.  Being deferred or shuttled into an RFP process with dozens of competitors is professional quicksand.

What to do?

  • Have a clear business or marketing objective at the center of your proactive proposals and ideas.
  • Understand the client’s calendar and use important dates and time periods as leverage.
  • Qualify the decision makers you call on before you call on them, and then again at the close of each sales call.
  • Make it abundantly clear to your salespeople that getting on the RFP is not a victory; define the goals for every client or agency meeting very specifically.
  • Look hard at the time and resources you’re committing to answering RFPs; the creative talent and resources you’re expending would be better used in smart, proactive approaches to customers.
  • Be ambitious and unreasonable. If you’re only trying displace the weakest vendor on the list or just get a chance to show your stuff, there’s no room for you anymore.  Go big or don’t go at all.

We’ve been talking about the demise of the RFP for over a decade. Yet it survives.  And it’s become the holding pen for sellers, technologies and ideas that should instead be getting active, urgent consideration.  Accepting its failed promise is the worst strategic decision any of us can make.


Moving the Chains.


You know what we could use more of in digital sales? Cause and effect. Intentionality. Some good old fashioned I did this and then they did that.

Instead — too often — sellers go through the motions of the capabilities presentation or the big idea pitch and then expect – OK, maybe hope – that an approval or an insertion order materializes somewhere down the line. What’s missing are the numbers on the yardstick… the measurable, incremental answers and victories that get us from here to the sale. As a result, sellers assign far too much value (and time and resources) to the presentation and not nearly enough to running a great pipeline.

Is your team asking the hard questions that would better qualify opportunities and decision makers? For the customer, there’s no upside in communicating a negative decision. Sellers have to work for the real answers. That work can begin with an Upstream Group sales workshop. It’s easier and more cost effective than you might imagine. And the consult is free. Reach out now to talk it over.

Great pipeline management starts before you even schedule time with the customer. Did they open your email? Acknowledge it?  Have we secured a meeting date? Is there an important date on the customer’s calendar that would create a deadline? 

And once we engage, a new set of questions starts to emerge. What’s the most this customer could commit to if this meeting goes well? What specifically am I going to ask her to do at the end of the call? What evidence do I have that this opportunity is either more or less likely than it was a week ago? What else might we try to learn to validate this opportunity?

Moving the chains on a commercial opportunity isn’t just a nice idea. It’s everything. Planning for the very next decision, the next yard marker, keeps the seller in the present. It tells him what he needs to close on in order to keep the deal alive. It prevents wishful – or even magical – thinking from creeping into your pipeline. It keeps everyone focused on what’s still possible and on making it more possible.

It’s sad when a seller doesn’t get the results and the outcomes that she’s worked hard for. But when she doesn’t even know what needs to happen next? That’s tragic.


The On-ramp and the Off-ramp.


As sometimes happens in our sales workshops, someone in the group tossed out a brilliant metaphor the other day. If I could remember who said it I’d give him or her the credit.  (If it was you, please go ahead and raise your hand to claim it – you deserve the notoriety!) With a little embellishment and polish from me, here it is.

A sales call or meeting is like a drive on the highway. The two most critical moments – the only ones that matter, really – are the on-ramp and the off-ramp. Survive these and the rest of the trip will take care of itself.

If you want your team to be terrific, make them specific. Speaking directly to customer needs is good business, and all it takes is a plan and some discipline. A strategic digital sales workshop with Doug Weaver and Upstream Group is easier and more cost-effective than you’d imagine. Reach out now. The consult is free.

Let me explain. The opening of your meeting – the on-ramp – is when you create a strong environment, set the agenda and truly engage and involve your customer. (Or… not.) Like the act of merging onto a busy highway, this moment demands that you be alert and decisive. You must speed up and create momentum while very intentionally finding your spot. At the very moment when this kind of decisive action is called for, too many sellers dawdle and meander through the opening of the call, wasting time and squandering trust with meaningless small talk.

Then there’s the end of the call – the off-ramp. This is the part of your journey that calls for careful braking… the part where you slow it all way down. This is the moment in the sales call where the thoughtful seller picks up most of the good information – where she truly qualifies both the buyer and the opportunity; where she identifies hidden decision makers and learns how she might get the deal done. But it’s at this exact moment when slow, deliberate and careful are warranted that many sellers speed up and rush through the close. As a result, they don’t ask for the sale and never get the chance to ask any of the important questions that follow – questions that could open up possibilities and close business.

The answer is surprisingly simple. Have a plan and practice it.

To hit your on-ramp at just the right speed, do some research and create one slide with a few headlines about your customer. Show the customer that slide and – before you say or do anything else – get them talking about it. You will immediately frame your meeting squarely around client needs while also immediately bringing them into a collaborative conversation.

For the off-ramp, write out and practice the question you’ll ask at the end of the meeting; a question that contains a verb (e.g. budget… approve… recommend…), a number (the amount you’re asking for) and a date (to activate the program, a start date, for the next commitment to be made). Role-playing the questions that follow (Tell me about how that decision will be made… Setting aside the outcome, is this something you’d personally like to see happen? … What other budgets might contribute to something like this?) is one of the very best ways a manager can support his sellers.

Open your calls quickly and decisively. Close them slowly and thoughtfully. And watch your numbers improve.