It never stops. Every day, there’s email.
Email automation has facilitated the flood of our inboxes. And for sales professionals, this inbox inundation translates into burned-out, hard-to-reach prospects.
All too often with email automation, quantity eclipses quality. It enables salespeople to quickly cast the widest net possible. However, from Saif Islam’s view as the director of enterprise strategy and sales at Boston-based WHOOP, a healthtech wearable, the best salespeople work on finding the right fit before they even write a first draft.
“Reps should be spending time researching a prospect to understand their needs. They’re instead using that time to send out ‘round peg, square hole’ emails,” said Islam. “When we value quantity over quality, email campaigns often lack relevance and are annoying to prospects.”
After a decade of the deluge, is it finally time to pivot away from email automation?
There are merits to slow communication in a fast world, and there are merits to a warm voice in a cold email. As Islam suggests, he would rather his reps spend time crafting a few exceptional personal emails than blast blanket outreach that lacks originality.
“As competition for attention intensifies, how can you craft a pithy, engaging email that catches the eye?” he asked.
Automation isn’t all bad; it has its place further down the prospecting pipeline. It is a great tool for follow-ups, administrative and support tasks. Used effectively, automation frees up time to focus on sales’ chief concern: building relationships.
Built In Boston sat down with Islam and two other local sales managers to see how email automation fits into their pipeline, and find out what tools sales professionals need to sharpen in its stead.
Dynatrace is an all-in-one software intelligence platform.
What have your most successful prospecting strategies been over the last few months?
Our sales teams work hard to understand the customer, their applications and ways in which our software can positively influence their business. We provide relevant communications to our prospects via persona target messaging with insightful data that helps tell a story. By executing a territory plan, our sales team understands our customers and clearly articulates the positive impact our platform would have on their business and end-users.
How much of a role should email automation play in a sales rep’s prospecting process, and what are the potential side effects of an overreliance on automated email?
Email automation provides our sales representatives with the ability to cast a wide net out to organizations that may be considering observability platforms. While email is great for a first touchpoint with a prospect, it’s not always the place to ask for a meeting without first earning that right.
If email is utilized properly, the rep becomes a trusted advisor to their prospects over time. Sales is about relevance, timing and understanding what the customer needs. One of the most important aspects of email automation is creating a message that makes prospects want to save your email so they can contact you when the timing is right. I’ve personally had prospects save my outreach emails and reach out a year later because the timing aligned, and they were ready to start seeing demos and evaluating platforms. Creating an email that a prospect can reference later is extremely valuable. That is why it’s important to ensure your emails are product use cases for their specific business challenges, big-name customer testimonials or info around their tech stack.
If email is utilized properly, the rep becomes a trusted advisor to their prospects over time.”
As automated email campaigns lose their potency, what skills should successful reps brush up on to continue to thrive?
Sales reps must ensure they are not only consulting on prospects’ short-term goals but also longer-term strategies. Expanding the big picture is critical to long-term partnerships with customers. If a prospect is going to make an investment in your technology, they need to know they can be confident in their technology decision. Originality is key, in addition to ensuring the messaging aligns with the buyer in each communication. One of the most valuable skills a sales rep should brush up on is their ability to research and understand their prospect or customer. This will not only prepare them to have meaningful conversations with the organization but also help stand out from the crowd, which likely follows a standard template for prospecting.
WHOOP is a health and fitness wearable.
What have your most successful prospecting strategies been over the last few months?
Our mindset starts with a focus on delivering exceptional value to prospects. We spend a lot of time building valuable content that we share publicly on our WHOOP Locker, on LinkedIn, in podcasts and other platforms. This has proven to be our most successful prospecting strategy, leading to a strong stream of inbound requests from organizations that want to learn more about the impact of biometric insights.
We have also had success through customer referrals. As an earlier-stage enterprise solution, we have the advantage of deep relationships with some of the most innovative leaders across healthcare, tactical, corporate and athletics spaces. These individuals believe in our mission and want to see WHOOP succeed. They have been critical advocates for us and we haven’t been shy about asking for them to introduce us to their peers.
Lastly, while we don’t believe in blasting out LinkedIn messages to everyone, we have had success with sending personal messages to individuals that have meaningfully engaged with our content or expressed pain that we can help them solve.
How much of a role should email automation play in a sales rep’s prospecting process, and what are the potential side effects of an overreliance on automated email?
Every organization is different, but generally speaking we don’t believe in mass email automation campaigns. Our reps use email automation to execute follow-ups and avoid rewriting some content, but mostly focus on sending hyper-personalized emails.
This is a slower and more time-consuming process, but we would rather our reps spend an hour sending three exceptional, personal emails than blasting out 50 generic ones. We measure outcomes over activity at WHOOP and have found this approach to produce much better results.
We would rather our reps spend an hour sending three exceptional, personal emails than blasting out 50 generic ones.”
Unfortunately, an overreliance on automated email would mean that we’ve neglected discovery at the prospecting stage. Every email we send out in the universe is a reflection of our brand forever, so we want to ensure each one adds value, is relevant and doesn’t feel spammy.
As automated email campaigns lose their potency, what skills should successful reps brush up on to continue to thrive?
The most successful prospecting reps understand that their discovery process starts from the first minute of prospecting. They block time for deep work and leverage the suite of sales software we have today to understand their prospects in depth. This ability to research is a skill that requires practice and repetition.
The next critical skill for reps to hone is their writing. Email automation means that it’s easier than ever to avoid developing this skill, but reps who write well immediately stand out.
Reps who write well immediately stand out.”
Lastly, some of our largest deals have come off the back of a brave sales rep reaching out to ask someone in their network for a referral. Making this ask is a skill –– you can practice role-playing this conversation with one of your teammates.
SmartBear is a suite of software development and quality tools.
What have your most successful prospecting strategies been over the last few months?
Last year many people changed their role within their organization or left jobs in pursuit of something else. I've found success by stepping back to review my accounts, identifying the point of contact I should be introducing myself to and setting up brief meetings with newly formed teams altogether. LinkedIn messaging is great for this.
Reaching out to new contacts felt like a fresh slate and a huge opportunity to understand new perspectives and engage additional teams within an organization. From there, regular touchpoints or check-ins on the calendar are key to being relevant, building a relationship and hopefully gathering referrals from an internal source to expand our footprint.
How much of a role should email automation play in a sales rep’s prospecting process, and what are the potential side effects of an overreliance on automated email?
It depends on the scope of customers or accounts the rep is responsible for. For me, I like to have control, maybe to a fault. So most of my strategic planning and prospecting is not automated until it gets to a point where I identify a relevant opportunity. At that point, I will source a larger scope of contacts and begin an automated and consistent message that is typically referencing a recent event or project. With larger opportunities, we have to be working and talking with so many people every day, so ensuring you’re hitting more volume is imperative.
Overreliance on an automated email is a wasted effort if you don’t understand what is going on within the account. If you're missing that, what problem are we helping to solve?
Overreliance on an automated email is a wasted effort if you don’t understand what is going on within the account.”
As automated email campaigns lose their potency, what qualities do successful reps need to continue to thrive?
Listen. I constantly remind myself that I need to hear the prospect rather than just trying to gain what I need to progress a sale. You will have a much better understanding of the gaps in their process, and from there can use it to share relevant content, product releases and educational sessions. Listening will also help you connect the dots internally with your prospect’s teams and leadership. You can map out your plan for outreach and share the issues you’ve learned about from other conversations.
I constantly remind myself that I need to hear the prospect rather than just trying to gain what I need to progress a sale.”
Recurring meetings help build trust and align with changing priorities. Those meetings naturally result in some non-work-related conversation where you get to know each other on a personal level and build a true partnership.
Lastly, our jobs have highs and lows. Stay focused on the work you’re putting in and finding what works. If your strategy or process isn’t getting you results, be patient and try something else. You have to be consistent to see a big payoff, so these go hand in hand.
