Pin the Tail on the DonkeyIs purchasing sales or marketing technology like playing Pin the Tail on the Donkey?

Marketing and Sales Operations departments are getting better and better at helping point salespeople at the best prospects as well as enable them with technology. Unfortunately the universe of potential technology partners, processes and vendors keeps growing. Over the past five years, the number of marketing technology companies has grown from just approximately 150 to almost 4,000. That’s a whopping 2,500% percent increase! MarTech’s new super graphic illustrates the sheer complexity of today’s marketing technology landscape.


As if choosing the right technology solution wasn’t hard enough, Sales and Marketing departments are also juggling challenges of CRM adoption, sales turnover, generating increasing amounts of content, searching for the “silver bullet insight” and how to better refine the Lead to Revenue process.

How does one prioritize? How does one create clear ROI’s for each initiative or piece of technology purchased?

It’s a little like playing Pin the Tail on the Donkey. Spin around three times with a blindfold and hope you get it right.

So how do companies remove the blindfold and pin the tail perfectly?

How do firms know which sales & marketing software is MOST impactful for accelerating net new logo acquisition and/or improving retention rates?

In my experience, one of two things tends to happen:

  1. Individual champions emerge from different departments trying to solve point solution issues that are impacting their area of accountability
  2. Companies become enamored with the buzz of a new VC backed company’s solution and get swept up in the cloud of excitement

“If companies ABC and XYZ are using this, then I should too” or “The ‘best practice’ analyst said this is great.” Don’t say you’ve never heard either of those spouted during a solution search phase before…

So what is the diagnostic that Marketing and Sales Operations should use to make purchase decisions?

Here are 10 questions to help your team evaluate the answer:

  1. How does this help me acquire net new customers? [Quantify expected gain.]
  2. How does this help me retain more business? [Quantify expected gain and/or loss avoidance.]
  3. Have I properly engaged the end user to review the User experience, to get buy in and agreement that this technology will actually deliver on #1 or #2
  4. Can this technology replace or ENHANCE other technology I am currently incurring?
  5. Do I have the proper process (and go forward resources) to make this product continue to run successfully?
  6. Is the technology elegant in simplicity, but robust in possibilities?
  7. Have I truly validated implementation and integration needs from both a cost and speed perspective?
  8. Is the vendors pricing transparent, comprehensive and simple to understand?
  9. Has marketing and sales jointly discussed the strategic objectives of this project in advance?
  10. What do we give up to add this?* (A sales rep, a secretary, a conference sponsorship, another piece of software we under-utilize etc.) * There is an argument that this is moot if you are in hyper growth mode and have a strong capital base.

Hopefully using this series of questions as a diagnostic tool can help you pinpoint where to put the tail and make smarter purchasing decisions for your company as a whole.

Ian Levine
Ian Levine is the Chief Sales Officer at RO Innovation. Ian has a depth of experience building go-to-market strategies and has purchased and implemented CRM and other sales & marketing technology while leading sales and marketing for Fortune 500 and mid-market firms.