How a Personal Touch Helps These Salespeople Thrive in an Automated World

With prospects quickly burning out on emailed queries, the sales pendulum is swinging away from automation and back toward old-fashioned tactics.

Written by Jeff Kirshman
Published on Feb. 04, 2022
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We all seem to have itchy “unsubscribe” fingers these days. 

Endlessly inundated with emails bearing questionable relevance or utility, our cursors frantically search for the antidote that delivers us from the clutches of incessant automated sales inquiries. 

The cold dispassion of automation only adds to the misery. After years of robotic assistants unleashed into the ether, the prospects on the receiving end of these messages are desperate for a healthy dose of humanity. 

“While automation helps the sales process and can create brand awareness, it doesn’t make up for personal touch,” said Tricia Shea, a strategic partnership advisor at fintech company DailyPay. “In order to be successful in prospecting, you have to be able to engage the prospect from the beginning.”

With the pendulum swinging away from automation and back toward old-fashioned sales tactics like phone calls and physical mail, it’s only right that we find solutions to the problem directly. That’s why Built In New York checked in with six local professionals to discuss how a personal touch can help salespeople thrive in an increasingly automated world. 

 

Image of Tricia Shea
Tricia Shea
Strategic Partnership Advisor • DailyPay, Inc.

 

What have been your most successful prospecting strategies the past few months?

Over the past few months, Dailypay has taken the time to build the ideal customer profile and send relevant content to each prospect. Sending them something of value and making sure to stay top of mind has been the key to success. It’s also important to use your network and educate the prospect as much as possible on how you can impact their business and their KPIs. 

 

What role should email automation play in a sales rep’s prospecting process?

I think email automation should be relied upon for familiarity of a brand, but it should not be the main source of prospecting efforts. Email automation is generic and not typically customized to the unique needs of each client. Relying on it too much could turn a prospect off and become more of spam mail than relevant content on the business impacts or industry trends. 

Email automation should be relied upon for familiarity of a brand, but it should not be the main source of prospecting efforts.”

 

As automated email campaigns lose their potency, what skills should successful reps brush up on to continue to thrive?

Successful reps should always be brushing up on a variety of skills to make sure they can thrive. One of the most important things they can do is make sure their cold calling and networking skills are strong. Knowing a company’s industry and the impact you can have on the organization are crucial. It is also important to use a personal touch and let people know how you can help them. No one wants to be sold to, so it’s important to gain trust and credibility early on, even when doing cold outreach. Never be afraid to reach out and educate your prospects on how you can impact their business and create your own opportunities.

 

 

Teachers Pay Teachers Team Photo Outside near a lake
Teachers Pay Teachers

 

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Keith Amirthalingam
Senior Account Executive • TPT (formerly Teachers Pay Teachers)

 

What have been your most successful prospecting strategies the past few months?

At Teachers Pay Teachers, our marketing and sales teams work together to outline and iterate on prospecting strategies for our school and district subscription, TpT School Access. Since 80 percent of teachers in the U.S. use TpT, the teacher referral pipeline has been a primary source of leads, where teachers refer their administrators to learn more about our subscription. Our marketing and sales teams connect weekly to analyze funnel performance and collect learnings to help us improve our sales pitch. 

Because time is a challenge for many administrators who are dealing with the impact of the pandemic, our teams have iterated over the past year to include some self-service options within our prospecting process. For example, we provide an option for administrators to watch a brief prerecorded overview video of our product demo, with the option to to request a quote or an extended product demonstration with one of our account executives. This resource ensures that we can engage busy administrators with email, and we are learning more about how to leverage video across our marketing and sales funnel.

 

What role should email automation play in a sales rep’s prospecting process?

Email automation is critical to a high-volume sales process and creates significantly more capacity for sales representatives when used correctly. Automated email cadences can be deployed across the sales process to generate volume that cannot be replicated at scale with manual emails alone. At TpT, our sales team leverages outreach, which allows us to create email and call sequences and pull in data from our customer relationship management software, Salesforce, to personalize the content of the email. This allows sales reps to be flexible, including overarching themes and nuance into their email outreach. 

Relying too much on email can be a risk, especially when we’re in the height of a busier season and pipelines are bloated. It’s important that you have regular checkpoints with email automation teams to ensure content is relevant and timely and that, for high-value contracts, you focus more on personalization in email. It’s important that we are speaking to customer’s pain points directly and our product is framed as a solution for their school or district.

Relying too much on email can be a risk, especially when we’re in the height of a busier season and pipelines are bloated.”

 

As automated email campaigns lose their potency, what skills should successful reps brush up on to continue to thrive?

At TpT, we work directly with school administrators and teachers who are dealing with the impacts of Covid-19 and learning strategies for remote and hybrid learning. One of our core values is “engaging with empathy,” which is especially important as an account executive. Since in-person interactions with our clients are limited, I strongly encourage sales reps to make the most of the time spent with clients while on Zoom or phone conversations and build their interpersonal skills. The discovery portion of the call should be a key area of focus, as we want to be able to gauge the goals and priorities early in our conversations to allow a more catered approach to the school’s specific needs. This helps with building trust early in the sales process and providing data points on how we can address their specific pain points. By doing this, even if we’re unsuccessful in some cases with initially earning their business, we’ve found that some schools factor our subscription product into future budgetary cycles or are open to conversations with us in the future.

 

 

Aerial photo of Happeo team outside on lawn
Happeo

 

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Neil Bhuiyan
Business Development Manager • Happeo

 

What have been your most successful prospecting strategies the past few months?

At Happeo, I use a multichannel approach to make personal connections with prospects. Email, mobile and LinkedIn help me personalize messages to feel less robotic, more thought-out and better-researched, especially when using referral campaigns to find suitable prospects to go after. Utilizing features like LinkedIn voice notes and video prospecting, or tools like Vidyard or Tella, help amplify this effect. Snail mail is also effective, because people don’t expect it in a digital age, compared to email or other platforms.

Use more than three channels and take five to 10 minutes researching your prospects. Using channels beyond LinkedIn, like Twitter, Facebook and Instagram, are great, since companies now have more business accounts than before, so your reach for prospecting becomes larger. With research, you’ll find out about company updates and annual reports for public companies that’ll show their strategy and what they’re doing the next fiscal year.

 

What role should email automation play in a sales rep’s prospecting process?

Sales is a numbers game, and reaching out to several people with personalized messages is both time-consuming and won’t get you as far. On average, it takes me around 16 touches to book a meeting and only six with B2Bs. 

Doing that many touches manually isn’t scalable, but an element of personalization and research is still needed. Using the Pareto principle, I would say keep 20 percent personalized and 80 percent templated, depending on the person you’re speaking to.

Still, just because you can automate something, doesn’t mean you should. With something unpredictable like social media, automating replies means you’ll lose any degree of accuracy. With content-based messages on the other hand, you know why someone signed up and can automate the message to an extent.

Just because you can automate something, doesn’t mean you should.”

 

As automated email campaigns lose their potency, what skills should successful reps brush up on to continue to thrive?

In sales, you need to take your pitch, vision and content and arrange it in a way that resonates with your audience. Copywriting shared internally, for instance, might not resonate with the audience you’re trying to sell to. 

With automation email platforms, A/B testing helps. Understanding data, identifying what’s performing best and then fine-tuning the messaging through iterations will improve future response, traction and click rates. I advise reps not to make big changes right away and instead make incremental tweaks before measuring them against a good data sample.

Asking for feedback is a valuable skill as well. If a prospect declines a meeting, there’s nothing to lose. So ask them, “What made you respond to that email?” “Is there anything that I can do to improve having more conversations with people like you?” At the very least they will feel valued, listened to and positive about your brand, which can lead to a future sale.

 

 

Image of Tyler Curry
Tyler Curry
Sales Manager • Chainalysis

 

What have been your most successful prospecting strategies the past few months?

One prospecting strategy we use at Chainalysis is to always be in tune with the most recent articles, tweets, content and funding raised in the blockchain and digital asset industry. We have Google alert keywords turned on, and when there is a relevant article or announcement, we look for the key people mentioned in the article. We then send a highly personalized message to that person and others who work with them. We also have blockchain/digital assets job alerts on, so if a company is hiring a crypto compliance officer, that is a strong sign they will need a data and analytics platform like Chainalysis. Anything we can do to provide the right information at the right time increases the potential success of our outreach.

 

What role should email automation play in a sales rep’s prospecting process?

Email automation should be used, but definitely not solely relied on. There are two key points to keep in mind. First, ensure you are reaching out to the correct contacts at the company. Make it a best practice to prospect your potential economic decision-maker, champion and evaluators. Second, in your messaging, portray the company’s presumed negative business consequences, provide evidence that your company can add value (e.g., customer testimonials) and finish with a positive business outcome (but don’t write about features!). We coach our reps to have a base of automation, but we always send out personalized messages to their top target accounts. This is especially true when they come across an article, tweet, job alert or fundraise about a company in their territory. I suggest looking up the relevant contacts at the company on LinkedIn, sending that individual a personalized message that pulls a sentence or phrase that is relatable from the article and then finishing with why you’re curious to learn more.

We coach our reps to have a base of automation, but we always send out personalized messages to their top target accounts.”

 

As automated email campaigns lose their potency, what skills should successful reps brush up on to continue to thrive?

Finding innovative ways to research, prospect and relate to prospects in a personalized message will always be key to getting that first meeting. I’ve always been a huge proponent of cold calling. Being able to pick up the phone and hear someone’s voice, tone, conviction, energy and enthusiasm will never disappear. People have been stuck in their homes for two years now and want to chat with others. If you find their number, call them and relate to them in the first 20 seconds of that conversation. Also, don’t forget about events. We’ll hopefully see in-person events begin to resume more often, but this can apply to other virtual events as well. When people are at events, they are there to learn, network and talk to people. Find out who is speaking or attending and set up meetings with them. They’ll likely be open to introducing you to their network if you can come across as having value to solve real business problems.

 

 

Eden Health team outside near a lake
Eden Health

 

Image of Dana Drake
Dana Drake
Senior Account Executive • Eden Health

 

What have been your most successful prospecting strategies the past few months?

We’ve seen many prospects become overwhelmed by the amount of automated outreach they receive. To counter this, I make sure to customize my communication as much as possible. I look on LinkedIn and use other tools to see what HR leaders — our prospects — are really looking for in benefit solutions and then tailor my communications accordingly. I also leverage relationships I have already built with current clients to ask for referrals. When our clients are on-boarded and can see the power of Eden Health, they are able to connect me to their peers in the industry and recommend our solution. A good referral helps to connect quickly with the right contact inside an organization. Just as importantly, it helps to start the conversation on a positive note.

We’ve seen many prospects become overwhelmed by the amount of automated outreach they receive.”

 

What role should email automation play in a sales rep’s prospecting process?

Email automation can be powerful when used purposefully. We use this strategy for helping us follow up after events and other instances where the scale would be difficult to manage on a 1:1 basis. However, there is only so much personalization that you can do with automation. All of our clients have unique challenges they are trying to solve. It’s extremely important to be able to explore those challenges and show how Eden can help solve those challenges throughout the sales process. This helps us connect with our prospects, shows prospects where we can provide value and leads to a more successful sales cycle. 

 

As automated email campaigns lose their potency, what skills should successful reps brush up on to continue to thrive?

I would break this into two categories. The first is building relationships. Even in a world where meetings are typically still happening virtually, building relationships with buyers remains an absolutely essential part of the sales process. It’s through these relationships that you can learn what the prospects biggest pain points are, what their current solutions look like and how their team is structured. Each of these pieces will help you navigate the sales process with them. You’ll be able to sell your product in a context that makes the most sense for them, lead a smoother negotiation process and set your program up for success in the long run. 

The second is having a deep understanding of your product. Understanding the intricacies of your product, including how your best clients are using it, will absolutely help you sell the product in a way that will set you up for success in the long run. At Eden Health, we unite primary care, mental healthcare, physical therapy and care navigation in one simple-to-use app. Showing employers how Eden’s new kind of primary care model has positively impacted their workforce through de-identified patient stories is crucial for demonstrating the value. 

 

 

Image of Reno Pieroni
Reno Pieroni
Regional Vice President of Sales • Zipari

 

What have been your most successful prospecting strategies the past few months?

I experience the most success when I inform and educate prospects with relevant content, webinars, conferences or industry news on a regularly biweekly cadence. This demonstrates some level of value that I personally can bring to them and establishes Zipari as a thought leader in the industry to build trust. Additionally, I like to share anecdotes on what Zipari is doing with our existing clients that may be of interest to them.

 

What role should email automation play in a sales rep’s prospecting process?

For me personally, I see limited value in email automation, as it struggles with establishing trust. We cannot move to a more value-based sales strategy without trust, which must be established at the first touchpoint.

I see limited value in email automation, as it struggles with establishing trust.”

 

As automated email campaigns lose their potency, what skills should successful reps brush up on to continue to thrive?

Successful reps should be able to identify and understand the internal and external challenges a prospect may be facing, and then use that information to shape their initial outreach. Making content accessible outside of an email, like an e-book, podcast or video, will help get your message across more effectively.

 

Responses have been edited for length and clarity. Images via listed companies and Shutterstock.