In today’s competitive B2B world, the strength of your outreach can make or break your sales pipeline and eventually play a key role in shaping your revenue growth curve. (And in case you’ve been living under a rock it’s because of the current health/financial crisis) The same dilemma plagues sales and marketing pros worldwide – How to balance personalized communication that builds real relationships with the efficiency of automated outreach that allows necessary scale. This balancing act of quality and quantity is one of the biggest challenges facing sales organizations today, they need to generate quality by targeting in a world where the buyer’s demands are increasing, but their attention spans are getting shorter and shorter. With inboxes inundated with generic pitches, decision-makers have built up both technological and psychological filters to prevent messages without relevancy or authenticity from getting through. But at the same time, a sales person is just never going to have time to write custom emails to every potential customer in their territory because they are expected to hit high, aggressive quota numbers. This ultimate guide will examine the capabilities (and the limitations) of personalization and automation in your outreach strategy, and give you actionable frameworks to decide what’s the proper mix for your specific business, prospects and sales goals.

Personalization in Outreach, the Case

What is prospecting Personalization?

Personalization in prospecting is not just replacing the placeholder in email template greeting with your prospect’s firstname. True personalization is actually creating a message that shows honest-to-goodness research and understanding about the recipient’s unique situation, pain points, priorities and opportunities. This involves tailoring not just one, but many parts of your outreach including the subject line, opening hook, framing up the value proposition, social proof selection, and even the tone and style to meet the recipient’s communication preferences or the style of their organization. Good personalization might refer to new company updates such as changes in leadership, funding news, company strategy, or challenges in a market that you’ve uncovered in your research. It could even reference a particular piece of knowledge that the prospect has shared in their content (i.e., a tweet, published article, podcast appearance) — signaling that your message isn’t just another mass-sent load from a database. The most advanced personal outreach shows that you you’re not only aware of who the prospect is, you have some interesting hypotheses about how your solution can solve their unique problems in ways that broadly available options can’t, which effectively pre-qualifies the match between what you’re selling and what they need before you even get into a conversation.

Advantages of Personalization

The numbers behind personalization The numbers behind personalized outreach are pretty overwhelming and consistent in all the research and benchmarks ps illustrating the great results brought in by the personalized campaigns. Emails that use personalized subject lines are opened at rates 26% higher than emails with generic subject lines, and personalized message bodies yield response rates that are often 50% higher than the response rates of non-personalized ones, according to several industry studies. Outside of these immediate engagement factors, putting in the effort to personalize messaging helps lay the groundwork for stronger, more trusting relationships from the get go by showing you care enough about the prospect to invest time learning about their unique situation, rather than just treating them as a name on a lead list. It all starts with one initial invest in credibility and rapport that will pay back dividends throughout the sales cycle by the way of a significantly reduced time-to-close and higher win rates against deals that were born out of less personable outreach tactics. Personalization also shows an incredible amount of research competency and buyer intelligence, and throws you into the bucket of being a smart potential partner vs. just another person trying to sell a solution, especially in complex B2B sales cycles where expertise is an asset decision makers use to select partners. Maybe most importantly, individual outreach makes it much more likely that your prospect will share your message with other folks in their organization — turning your initial contact into an internal champion who carries the message into places you can’t go.

Optimal Use of Personalization

Returns are the most impactful when you deploy personalization geared toward the larger strategic plays, or when the style of an account or group of accounts is so high that the additional time spent digging in and crafting messaging at a more personal level is worth the investment. Target accounts you have determined through ABM approaches to be of high value require the higest degree of personalization, as you have already qualified these organizations as great matches for your solution based on qualification criteria, such as revenue potential, strategic fit, and alignment with your solutions. Another such group is latter-stage leads that have engaged substantially with your marketing material or site and for which personalization can have a big impact on conversion rates as interaction history can be exploited on a per-case basis to fine-tune automated message to directly tackle those topics or features that aroused your visitor’s interest. Personalization is even more essential in enterprise sales, where you’re likely to face multiple stakeholders and a complex buying committee, all of whom have different priorities, pain points and evaluation criteria that cookie-cutter messaging won’t cut it for. If they were referred to you, or somebody you both know introduced you, signaling them as just another business card to get tossed into the pile is an insult to the universe for helping you make that connection, and a waste of the social capital laid out by the friend who provided a referral in the first place. So, in a highly regulated industry, in a specific technical environment, or with a special set of compliance needs, you need to reach out in a manner that shows that you are aware of the constraints that they are under, and that they your solution can help them meet those constraints. And you aren’t going to get that with a template.

The Benefits of Automating Your Outreach

What Exactly is Outreach Automation?

Outreach automation is the tech, platform, and workflows that sales orgs use to systematically coordinate outreach across a large group of prospects, in a way that doesn’t require a human to activate every individual message or touchpoint. At the heart of automation technology lie the ability to build predefined message sequences assets that can be deployed across a wide array of channels (e.g., email, social media, SMS, even voice) at the time that rules have been set and the right triggers occur. Contemporary tooling like Apollo, Outreach. io and SalesLoft includes powerful workflow automation far beyond normal message delivery scheduling that allows such things as sequence tree branches based on prospect behaviors and actions, trigger and create a task for a sales rep to take an action where manual intervention would be beneficial, and, the integration with CRM to drive full outreach and response documentation within the customer record. Also these platforms often provide rich analytics which measure performance of different versions of a message in campaigns and allow for data-driven optimization through systematic experimentation and iteration. The most sophisticated automation tools include AI, which revolutionizes automation beyond just simple drip campaigns and open rates: AI capabilities today can include send-time optimization (which delivers those emails when a recipient tends to prefer an open, based on history), content recommendations that suggest what the performance data tells you should be included, and even automated scheduling of meetings that cuts out the back-and-forth of calendar coordination once a prospect shows interest in talking.

Benefits of Automation

The most obvious advantage of automation is its unlimited scalability: Your sales team can be reaching out to thousands or tens of thousands of prospects all at once, without adding more staff or resources. This exponential increase in reach allows companies to quickly test and enter new market segments, geographies or vertical industries which may otherwise go untouched due to bandwidth limitations of manual methods. The time savings generated from automating this gets converted into increased productivity in sales organizations by removing sales reps from glorified admin work and enables them to apply their skills to where it counts more — discovery calls, presenting demos, overcoming objections and navigating the highly nuanced terrain that is compensation negotiation (where human judgment and negotiating skills can have the largest effect on revenue). Automation also adds a level of consistency to outreach processes that wasn’t available before and guarantees best practices are in place with every team member without sustainment on habits or tendencies - a popular feature when scaling organizations with reps at different levels or when branding is an important part of the strategic goal. From a management standpoint, centralized control granted by automated systems also gives privately held companies much-needed visibility into outreach activities – and the resulting outcomes – via best-in-class tracking and reporting capabilities that allow leaders to easily spot underperforming campaigns that need tweaking, as well as success tactics that warrant replicating across the organization. Perhaps most importantly, automation allows truly advanced testing strategies that can be deployed to scientifically maximize every aspect of outreach from subject lines to call-to-action language through data-driven, high-volume experimentation resulting in better and better performance over time – performance that could never be accessed when relying only on intuition-based approaches.

When to Use Automation

The most value automation delivers is earlier in the sales process in your prospecting efforts, where the “goal” is to sift through a significant list of people/contacts that could be interested based on a rough profile that meets some basic criteria, but have not necessarily raised their hand to say they are interested in your offering. List successions of sequenced emails that target people who have something in common, i.e., if they belong to the same industry, company size, role, use the same tech, geographical location etc. to achieve some amount of reasonableness and relevance without personalized value for this cohort. Lead nurturing campaigns that help to stay top of mind with the not-ready-to-buy-prospects that likely will be ready to purchase someday, is a great place to deploy automation since they require a cadence which is not feasible if one had to manage it manually. Programs that are built based on engagement triggers (like downloading content, attending a webinar, visiting a pricing page, etc.) tend to work well based on automated email follow up a short while later than building something to receive manual outreach that might get delayed because of other priorities or geographic time zones. Automation can also take care of business as we often think of routine communication before and after critical stages in the sales cycle – confirmation and pre-call prep materials sent before a demo, for example — a few minutes at a time add up during the course of a week.

The Dangers of Going All-In on Either Direction

Over-Automation Risks

Reception is in most cases automated and devoid of human touch, as a result, the contact immediately assumes that is receiving a universal message, processed by the (already known) filtering psychological and telematic system that is more use to commercials. In truth, this perception significantly lowers engagement by all the normal measures—open rates, response rates, meeting conversion—together with increasing negative outcomes like unsubscribes, spam complaints, and irreparable harm to the email domain reputation that can put deliverability for the entire organization at risk. Anyway, even if broader performance were not a concern, over-automation is a good way to shoot your brand in the foot and boot itself out of the market, especially in industries or buyer personas that heavily value relationship quality and partner attention (prospects who receive what’s obviously a templated outreach often assume they’re going to get the same impersonal treatment if they ever became a client). Representatives who only work through canned responses tend to have a shallower understanding of what a prospect needs, what they’re struggling with, or what they’re objecting to compared to reps who are having real conversations—and even if the prospect and rep are live, this is leads them to having poorer consultations. But just as concerning as all the above from a strategic standpoint is the fact that companies that rely too heavily on automation typically ratchet up their behavior over time as their performance numbers start to soften, often resorting to adding volume or tweaking message frequency, or using bait-and-switch subject lines—all gear that can contribute to a sort of death spiral of bad returns and brand damage that’s very tough to pull out of once you’re in it.

Dangers of Over-Personalization

At the other end of the spectrum, investment in highly individually customized outreach for every prospect – regardless of fit to customer profile, or potential value – leads to a hard volume cap of the market and generation capacity compared to competitors who take a more efficient approach. Extensive time commitments associated with thoughtful research and message customization often contribute to sales development burnout, causing reps to struggle with not only maintaining the volume requirement, but, also, to keep quality as high as required when the job becomes simply impossible to do at a personalized level that equals and/or exceeds sales targets. “One-size-fits-one” plans relying solely on individual representative effort most often lead to disjointed execution throughout the salesforce, with their inherent differences in talent, experience, and diligence resulting in wildly discrepant performance depending upon which team member has responsibility for a given account or geography. Over-personalization’s accompanying perfectionism leads to unfair timing gaps in executing outreach, for example, reps missing important market openings because they won’t send out a non-perfect message or procrastinating about reaching out to strategic accounts because they don’t feel fully prepared.