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The lost art of selling in real time

Mike Braendel

Updated: Oct 4, 2021




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The role of sales outreach for lead generation has evolved significantly since I first entered the high-tech industry as a selling and marketing professional. Now, as a seasoned consultant with a strategic perspective focused on driving quality sales pipeline, there is no denying the effect of disruptive change. The pandemic has accelerated the trend of using remote selling teams to develop leads and sales opportunities.


Selling Technologies Always Go Back in Style

Any medium for sales outreach will always be dictated by current accepted practice while being influenced by newer technologies as they become adopted. As the phone was eventually augmented by email, newer capabilities available on social channels via LinkedIn Sales Navigator, Twitter, Instagram and Pinterest and others are finding steadily increased adoption.

That said, most of my peers would agree that finding ways to combine all of the above approaches has the best potential to yield results. Consequentially, I include things like connection via email conversations and LinkedIn dialogue data in my reporting back to clients.

While social activities and appropriate content has their place in today’s selling outreach, unless they involve an engaged real-time conversation between an outreach representative and a prospect, I feel they are primarily supportive activities. Incidentally, when trouble-shooting core issues related to program and seller performance, I look at activities that are KPIs for engaged conversations that “progress the sale”: dial volume and connected conversations (which I call “connects”), then conversion rate of “connects” to qualified leads.


Conversations vs. Messaging

My mantra has always been “if you are not talking to enough people on a daily basis, nothing else matters”. This means I emphasize daily “conversations” over anything else when talking about key performance indicators. In a world faced by all types of daily disruption, the need to have relevant real-time conversations perhaps matters even more.

What key factors drive connection rates beyond call and email volume organized into a cadence or sequence? Target market identification, personas, ideal customer profiles, lead list quality, and relevant messaging. Assuming you already have identified and have a way to target contacts that can uniquely benefit from your solution, and you execute the appropriate messaging, the next step to consider taking is to make your outreach operational is to improve the quality of your contact list.

Gone are the days of digital outreach only (at scale anyway) and trying to reach contacts without a direct number or cell phone. There are exceptions, but if you are trying to sell a complex product into a large enterprise company, it’s almost a non-starter.

Once you attain a minimum threshold of reasonable productivity (25-30 connected conversations per week) by using a quality list and relevant messaging rolled up into a consistent and persistent outreach pattern (cadence or sequence), what is your next step towards best practice? Having your team spend all of their time calling warm/hot leads from marketing is one way, but that is often difficult to sustain, time consuming, and expensive.


Team Up with Agent Assist Dialing

From a cold outreach perspective, one method that continues to gain traction in today’s uniquely disruptive environment is to engage agent-assisted dialing – using a team of callers that do the dialing for you and connects the seller when the contact answers.

I tested this technology a few years back and my opinion towards it then was “it’s another tool in the toolbox that may not fit all sellers’ tastes”.


Changing the Game – Using Crisis as Opportunity

Based on today’s widely accepted fact that it now requires many more touches to a “buying center” within an organization or product evaluation team to convert leads into real opportunities, I would now argue that agent-assisted dialing is a definite must have. The 2020 pandemic and disruptions to both vendors and customers has made it a definite game changer!

My coaching sessions with my sellers are no longer around “how do you go from only speaking to 1-2 people a day to 10+? “

In the last few months, the dialog has instead shifted to “how do you sustain that connection rate (via list quality) and convert more leads (via sales enablement) from your live conversations?”


“Connecting” the Dots in a Digital Marketplace

I ran a complimentary pilot with Connect Leader for one of my high-tech clients back in July of this year and the two sellers had 87 real-time conversations in 2 days, generating $350K+ in validated sales pipeline within two weeks! I have never seen a tool perform that way in a pilot…. ever.

The client is now using the Connect Leader platform on a daily basis, with the sellers mostly focused on progressing leads to opportunities as the tool allows them to connect with up to 20 contacts for ~2 hours a day, freeing up more selling time.

With this change in KPIs the focus has shifted to determining which leads to nurture and/or advance in the sales cycle based on client qualification criteria.


Connect Rate Success Chart

To ensure your sellers are optimizing for the best connect rate and quality conversations that drive the best sales opportunities possible, I recommend the following:

  • Have a quality list of the:

    • Right personas

    • Accurate email addresses

    • Direct phone or cell numbers


  • Messaging:

    • Is content focused around contact needs and value proposition?

    • Nail your opening

    • What’s the ask? Meeting? Review digital content?


  • Understand the burn rate of your list to avoid “valleys” in productivity:

    • How many times to hit the list?

    • How long will it take to complete the list?

    • Know ramp time for the new lists/campaigns


Progressing the Sale (while facing today’s unique disruptions)

Sales outreach to generate pipeline is facing disruption from multiple fronts. First, larger evaluation teams are increasingly hard to reach due to their numbers, mobility, and distributed work locations (accelerated by the Pandemic of 2020). Second, the fact that content creation continues to accelerate and more ways to connect via selling applications are providing more ways to engage prospects. While these trends will continue, they are also contributing to environments where a conversation is needed to move a prospect forward beyond the level of marketing engagement (via digital content and apps alone).

To optimize for the aforementioned disruptions, personal dialing agents take care of the busywork required to dial, navigate phone systems, and even talk with gatekeepers to get you to your target decision makers.

Once your agent has reached your contact(s), they instantly hand off that live conversation to your salesperson in a seamless process that is invisible to your prospect. It is equal to having many human personal assistants making your calls and then handing off the live connection to your seller so you can focus on having conversations, instead of wasting your salesperson’s time dialing.

Getting sufficient numbers of leads qualified will never be easy and contacting both warm and cold leads with any new technology to meet business objectives will offer mixed results. While savvy use of quality lists, differentiated messaging, and modifying your approach to various audiences via multiple channels (including social) will get you part of the way, “progressing the sale” to a quality opportunity will require engaging a prospect in a real-time conversation. As sales outreach becomes increasingly harder to attain at scale in these trying times, consider how your team’s success rate might increase by talking to 2x or even 3x more prospects in a sales day by using an agent assisted dialer to super-charge your outreach efficiency.

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