12 Obstacles Between You and Outbound Sales Success

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John Girard
John Girard



Here’s an interesting thought exercise: how many separate problems do you think you have to solve in order to get outbound sales to work? And what are your chances of solving each of them immediately?


The answer to the first question is pretty scary. Even if you have strong evidence of product/market fit -- and a sales process that can close business at a predictable rate -- there are actually 12 other discrete problems that still need to be sorted out to get from zero to your first outbound sale.

I know this because not only am I CEO of CIENCE, a company that specializes in helping the sales teams we work with build long-term client relationships, but I’ve run right into all of these problems myself while learning how to conduct successful outreach.

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Complicating things further, all 12 of the problems are related but discrete problems. Your ability to solve any one of them doesn’t necessarily predict your ability to solve others.

Worse, in order to get this type of outreach strategy to work at scale, you must solve each problem -- not just a few of them.  A “zero” or “unsolvable” on one could mean a zero result on outbound overall.

As a result of the “failure to solve one-step means failure to finish” dynamic, the math is simple. Let’s say you have a pretty good team and an 80% chance of overcoming each obstacle. In that setup, your chance of getting outbound sales right the first time around is a whopping 6.9% (.80^12).

What seemed like a simple problem (e.g., “Let’s reach out to people who look a lot like the customers we already have and start a conversation.”) is suddenly not so simple.

Fortunately, these 12 obstacles are all surmountable. I can say that confidently, because we overcome them every day on behalf of all of clients. Here’s the way we think about them.

The reality is there are actually six discrete problem “categories” each of which has a zero to one (“Can I make this work at all?”) and a one to n (“Can I make this work at the scale I need?”) component. Below are these six problem categories and the obstacle for each.

Outbound Sales Mistakes

1. Sourcing the right leads

    • 0 to 1: Once you’ve identified your ideal customer profile (i.e., you’ve figured out exactly who you’d like to speak with), search the internet for anyone else that fits the profile and identify ways to connect. This is harder than it seems, as many prospect segments have constituents that don’t identify themselves on LinkedIn or in other social channels. Once you’ve found a lead, the task of finding a matching email and/or phone number is next.
    • 1 to n: Assuming you were able to find just one or two prospects matching your ICP, the question remains: can you find hundreds or thousands more? And through what sources would you find them, over how much time, and for what resources expended?

2. Delivering and connecting

  • 0 to 1: Assuming you’ve solved the first problem and identified your leads and their contact information, decide if you can engage them in a channel that catches their attention. This means connecting with them on the phone or in their inbox.
  • 1 to n: Solving the email deliverability or phone pick-up problem once doesn’t mean it’s solved at scale. That’s where a new set of challenges await, including domain reputation and email deliverability issues, phone dialers, and refined scripts.

3. Engaging

  • 0 to 1: Getting in your prospect’s inbox isn’t enough. The right subject line compels a prospect to open and read; the right copy compels them to take positive action. The right mix of timing, target, subject line, copy, and call-to-action must align to get a response. And until you hear from them, you have no idea how you’re doing.
  • 1 to n: Once you’ve gotten a result, the question becomes: “How can I achieve consistent results across multiple reps, campaigns, and touches over time?” Carefully measuring what’s working (and what isn’t) is the key to success here, and it’s nearly impossible to measure activities when they aren’t consistent.

4. Finding the right people

  • 0 to 1: The average salesperson sends over 100 messages a day. The most effective SDRs are smart, congenial, and hungry -- and most companies hire the wrong person for the role at one point or another. Getting the right SDR in the seat the first time is difficult.
  • 1 to n: Even once you’ve figured out what kind of employee makes the best SDR for your business, sourcing those candidates as you scale can be incredibly difficult, especially when you consider varying performance and employee churn. Most strong sales teams are perpetually hiring SDRs because they want to scale and need to deal with SDR attrition.

5. Training people

  • 0 to 1: SDR’s should formulate a successful campaign approach but will also likely discover they hit diminishing returns quickly. That’s because the techniques that worked three months ago are likely to be different this month, and an SDR who isn’t consistently learning new techniques and tools won’t be able to deliver over the long term.
  • 1 to n: This problem of SDR education is even more difficult at scale.

6. Getting the handoff right

  • 0 to 1: Once an SDR has successfully engaged a prospect and set an appointment, the sales process is almost ready to start. But huge questions await: Will the prospect show? Are they the right contact at the target business? What are they expecting out of the call? What does the sales rep know about the prospect before the call and how do they handle the transition between SDR and rep? Without scripting this carefully, “lost in translation” turns quickly into “lost opportunity.”
  • 1 to n: At scale, mastering the handoff from SDR to sales rep is even more critical, because small changes to the conversion rate can have huge downstream effects. For instance, is the SDR using best practices for setting the appointment (getting affirmative buy-in) and using an appropriate reminder cadence? How are no-shows handled? How does the end of the SDR “script” dovetail with the beginning of the sales rep script? This is probably the part of the process that gets the least attention (an appointment is an appointment, right?). Getting it wrong is painful because this is the step closest to opportunity development and eventual sale.

As you can see, solving the entire outbound sales puzzle is not easy. At each step, the outreach team must prove the step can be done once and then economically at scale. Failure at any one step means outbound fails.

Fortunately, there are rigorously tested, data-driven tools and techniques to help achieve success at each step and give your team the best chance at outbound success.

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Topics: Inbound Sales

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