Strategic selling is about engaging early at the most senior levels and some of these tips can help in that regard.

If you’re late to the dance, many of these ideas may spark ideas to execute before choosing to simply qualify-out.

1) The Intercept

The prospect is just about to buy so you could call this the perfect storm of compelling event meets multiple trigger events. Combatively, you demonstrate the value of your solution seconds before the photo finish and steal the ball aka the deal right out of the jaws of the competitor. It’s risky but if you can spot a flaw or establish FUD (fear, uncertainty and doubt) it can be leveraged. Savvy executives can be susceptible to ambivalence and will often kick tires the hardest in the 11th hour. Many software vendors combat this with price drops but the more sophisticated play is to position your solution on value. The intercept can shorten an 18 month sales cycle down to mere weeks when executed correctly, especially if this is an existing account and the need is NOW.

2) The Hail Mary Pass (or Kick)

Lob a call into the CEO’s office, make their EA your best friend by giving them the respect of an authentic pitch, and leverage this demand creation to schedule an on-site meeting between your own CEO and theirs. This takes boldness, courage and selling internally to get buy-in. The true wingsuit base jump here is to land the 1-on-1 yourself. (Combine #3 + #4)

3) The VITO Envelope

Send a plain manila envelope by courier with a one pager inside, hand addressed to the key executive and signed. Another way to execute this is via FedEx delivery to the Very Important Top Officer (VITO). They’ll typically always read these because it’s so rare. The letter sets-up a follow-up call. More tips on the structure of the letter in the Anthony Parinello classic. Paragraph one, WIFM, what’s in it for them: move from value proposition to value creation. Lead with provocative insight and demonstrate you’ve performed thorough due diligence of the business issues.

4) The Neighborhood Technique

Book your ticket to a key city in your territory. Then e-mail your prospect that you’ll be in the area. Schedule multiple “neighborhood” on-sites or leverage this technique to book meetings around a conference. This is most effective one week out.

5) Conference Within The Conference

Reserve a meeting room in a classy hotel across the street from a major conference. Schedule a dozen appointments over a couple days with key executives. You can leverage this to replace an entire quarter of on-sites. The executives are already there! The other ingenious method is to get a free floor pass, diagram the entire multi-level conference floor blueprint out and then strategically approach every single relevant booth moving past the greeters in front to the executives in back. Goal yourself to collect 300 business cards, shake every hand and add them all on LinkedIn with a personalized invitation; keep a running log in Evernote. (Ideal strategy for Dreamforce and OpenWorld).

6) Head To Head Pilot

If you truly have the better solution, challenge the incumbent to a fulfillment duel. Commence bake-off: may the optimal solution that drives the greatest efficiency win! Make sure you agree upon fair success criteria and eliminate any inequities or handicaps. It must be an apples to apples comparison in your apple pie contest.

7) The Full Blown Referral

Bold move but put their key decision makers directly in touch with your biggest client. YouTube video testimonials can be a fall-back. Believing is seeing!

8) The Reverse RFP

Build an RFP criteria document that realigns your strengths based on the selection criteria and question-set. Offer to provide prospects free consulting on the RFP process to ensure they are asking the right questions. Tip the scales in your favor.

9) “Your Baby Is Ugly”

Candidly level with them on what is broken by diagnosing their problems before hand. Be honest about how dire the situation is. Nobody likes to admit their “baby is ugly” but in business, it’s refreshing and highly ‘Challenger Sale’ to respectfully call out the elephant in the room of a missed quarterly target, flawed network architecture, broken website or fatally flawed SFA.CRM implementation. Hint: read between the lines of the annual report.

10) Walk The Halls

With an existing account, literally take a desk in their office, post-up for a day and get to know everyone in the building. Walk the halls and hang out at the water cooler. Without exaggeration, I’ve seen this technique work selling into finance where relationship building is still crucial, especially in key account management.

11) Be Over-The-Top Remarkable

I saw a top sales executive out-dress everyone in flawless suits, ties, pocket squares and shoes you could see your reflection in. Peacock much? Well, that was his thing and he authentically owned it. I saw another salesperson who was an expert at swing dancing who would clear the middle of the dance floor at company hosted client events. Another way to be remarkable is to recommend an idea that is fundamentally transformational to their business model. Push the envelope. Be willing to leave bright shiny collateral behind, like a massive poster board with a Vizio diagram of your latest collaborative brainstorming session. #unexpectedvalue Brian Lipp writes in,

12) The Ensemble Close

Be the conductor of the symphony. Despite the size and stratification of this global firm, a top performer at a software automation company won huge deals by looping in almost every conceivably party in the selling organization, even the CEO and CTO. Much to the chagrin of lower performers, so many stakeholders on both sides were invested in the deal, it became a self-fulfilling prophecy it would close and the deal even grew mid-closing! That guy always got the top performer award at every kickoff. (Not so coincidentally, he was also the aforementioned King of Swing!!)

13) Ghost Protocol

One of the people I am mentoring is achieving amazing sales results and in my view it’s because he has gained the trust of his own CEO to the point where he is leveraging the CEO’s LinkedIn account. This takes significant trust from the CEO but is a great example of achieving maximum support internally as you then go into the marketplace at the highest possible level with an ‘insight’ and VITO-style of approach. Another mentee unleashed a ghost army via a stealthy B2B lead gen startup that leverages an AI engine to effectively generate a dozen warm C-Level intros per week, skyrocketing fresh pipeline so sustainably, it’s temporarily supplanted the need for hiring an analog inside sales team to augment it!


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Tony Hughes
Tony Hughes has 35 years of corporate and sales leadership experience having generated record-breaking results as a salesperson, head of sales, and CEO leading the Asia-pacific region for multi-nationals. He is a best-selling author, consultant, trainer and keynote speaker. Tony is Co-founder and Sales Innovation Director at Sales IQ Global. He serves on advisory boards and has been published by The American Management Association. Tony has also taught sales for Sydney University, University of New South Wales, and within the MBA program at the University of Technology, Sydney. He has been ranked #1 sales blogger globally by both Top Sales Magazine and Best Sales Blogger Awards. Tony is ranked a top 3 sales expert and thought leader globally by LinkedIn and the most read person on the topic of B2B selling within their platform. He has more than 500,000 blog followers and has been rated the most influential person in professional selling within Asia-Pacific three years in a row. His first book, The Joshua Principle – Leadership Secrets of Selling, is in its 10th printing and his most recent books, COMBO Prospecting and Tech-Powered Sales are published by HarperCollins Leadership New York. Tony speaks at conferences internationally and his clients are some of the best-known brands in the world including Salesforce, Grant Thornton, SAP, IBM, Flight Centre Travel Group, Adobe, Siemens, Docusign and other market leaders.