Outbound Sales Development:
Prospecting & Cold Messaging Techniques

Morgan J Ingram has built an iconic brand in the sales world. Twice named to the LinkedIn Top Sales Voice list, Morgan helps SDRs through his content on LinkedIn and his podcast, The SDR Chronicles. As the Director of Sales Execution and Evolution at JBarrows , Morgan helps improve sales programs.

As buyers become increasingly aware of outbound sales outreach, SDRs must adapt.

Generic, templated emails or outbound calls to a large list of potential buyers 5-10 years ago was a convenient way to reach out to as many prospects as possible. 

However, today’s buyers have much more control over their buying process and do more research before contacting sellers.

Outbound lead generation is harder than ever for inside sales and business development reps.

Instead of the mass outreach of the past, today’s SDRs need to be dedicated to the quality of their cold messaging and the authenticity of their outbound sales prospecting techniques.

However, it’s not just the SDRs that have to adapt. Managers must evolve too.

Instead of relying on traditional methods and focusing on the number of SDR activities per day, managers now have to put more emphasis on the quality of activities and how SDRs perform.

With markets becoming more competitive and buyers continuing to evolve, the entire sales development team has to adjust to survive in today’s outbound sales environment.

Modernizing Your Approach to Outbound Prospecting

Today’s buyers do more research themselves, rely less on sales reps to influence their decisions, and connect with vendors further down the funnel than ever before.

This evolution in buyer behavior is pressuring sales development professionals to change their sales prospecting methods and put more energy into remaining relevant with buyers.

SDRs have to be smarter, savvier, and more creative than ever before to get a meeting, going above and beyond across multiple channels like outbound calls, emails, and even social.

Sales Development is Getting Harder

There’s so many obstacles for the modern SDR that didn’t exist in the past.

For example, think about the laws in place to abolish robo-dialers. It’s a win for consumers, but represents an obstacle for SDRs who relied on those to get enough activities completed.

Data legislation, email spam filtering, and how buyers respond to calls, emails, or digital messaging are a few of the many factors impacting today’s outbound sales environment.

To survive and sustain performance, sales development programs need to find ways to be unique, creative, and combat these changes.

Now more than ever, reps who are multi-threaded and unique will see themselves succeed against colleagues who can’t adapt or stick to old practices.

SDRs Need a Multi-Threaded Approach

Being multi-threaded (using multiple channels) is a must for any good SDR today.

Your outbound sales prospecting techniques must be adaptable because traditional channels are no longer as reliable as they were in the past.

SDRs who augment their phone and email outreach with channels like social, video, or direct mail are seeing more success and generating more conversations in this modern environment.

If you don’t know the best way to connect with your prospects, you have to test a handful of channels as a cohesive strategy until you start seeing results. 

The most successful companies and SDR teams are building outbound sales processes with multiple touches across many channels to make sure they’re effectively connecting with buyers.

It’s a perfect time for your SDR team to be testing new channels and outreach methods to better get in touch with your prospects.

Don’t Be Afraid to Be Creative

A major roadblock to modernizing sales development is the risk of taking on new channels, approaches, and ideas.

You aren’t going to find the perfect combination of channels right away. You should explore the different ways you can resonate with buyers and capture the attention.

For example, LinkedIn video and voice messages are a recent, lesser-used channel that’s enabling SDRs to generate abnormally high response rates.

A few years ago these channels would have never been touched, but are now becoming commonplace as SDRs test new and creative ways to get in front of their target accounts.

Companies and managers are often afraid of new channels because deviating from the norm is uncomfortable. However, adaptability is a must in this modern environment if you want your SDRs to remain relevant and effective.

Getting Unstuck on Outbound Prospecting

Change is always easier said than done. 

Some organizations are resistant to change because what they’ve been doing has worked well in the past.

It’s hard to tell someone that the success they’ve seen won’t continue when there’s been no indication otherwise.

However, historical performance doesn’t guarantee future prosperity. As buyers and selling environments evolve, outdated processes can leave you stuck as the world moves around you.

It might take a philosophical shift, but every organization needs to invest in modernizing their approach to sales development so they can survive, thrive, and outcompete as things change.

Overinvesting in the Same Approach

When organizations see success with a particular sales development approach, many tend to double down and continue using that process on a larger scale over the long-term.

For example, an SDR showing success with 100 dials a day might have their quota increased to 150 or 200 per day or another SDR hired to do exactly the same thing as the first rep.

While doubling down can be effective in the short-term on a smaller scale, overinvesting in a single approach can dig your team into a hole and risk you losing control over future outcomes.

It’s not that doubling down is an ineffective strategy. However, current buyer behavior and sales environments are demanding that outbound sellers be adaptable and creative.

Sales Should Constantly Evolve with the Environment

As buyers adopt new channels, research methods, and buying preferences, organizations have to keep up with these changes to stay relevant to prospects over time.

Sales is a profession where you can’t rest on your laurels. It’s vitally important to learn and apply new things every day to ensure success.

Unfortunately, adaptability is where a lot of sellers falter.

Your approach might not be wrong, but failing to evolve or adapt an existing strategy could set you back against the competition and push your program in the wrong direction.

Even if you’re doubling down and seeing awesome results, you still have to remain observant and evolve as changes emerge.

Merging New Ideas with Existing Processes

Despite this need for adaptability, it can be difficult to convince seasoned salespeople or sales leaders with decades of experience to evolve the organization with the industry. 

If they’ve been doing sales consistently for 10, 20, 30 or more years, why would they want to change the status quo and learn something new?

There’s bound to be resistance like this to adding new channels, tactics, and approaches to an existing process, even if that existing process isn’t very effective.

Unfortunately, people naturally resist change and comfort naturally prioritizes growth.

Leadership can help to buy-in and promote change within the organization. Innovative minds from leadership can introduce new perspectives, help implement change, and work with resistant reps to ease them into the new process.

Give freedom to reps who have been successful for the past 10-20 years, but don’t be afraid to introduce new concepts or channels that they can use to improve their existing process.

Outbound Prospecting Automation Vs. Personalization

The quantity vs. quality conversation in sales development can be felt more tangibly in the push and pull between automation and personalization. 

Too much personalization can be just as detrimental as overusing automation, so it’s essential to understand how to balance personalized messaging with automated outreach.

Automation is No Longer a Quick Fix to Performance

Automation is often heavily relied on for outbound sales prospecting.

Over the past 5-10 years, automation became a great way to scale outbound sales and give SDRs the power to touch more people, generate more conversations, and automate busy work.

Conversion ratios for sales development were often linear in the past, which means that reaching more leads with more automation would translate to more meetings and revenue.

This rule of thumb has been flipped on its head.

Because everyone can automate, prospects are constantly inundated with cold emails and cold calls.

Automation goes wrong when reps blast out emails or make outbound calls just for the sake of hitting their daily minimum. Treating sales development like marketing (one-to-many) instead of sales (one-to-one) is the downfall of many teams relying on automation.

With buyers changing how they interact with outbound sellers and cold messaging, there is a clear buyer preference for SDRs that take the time to personalize.

Instead of following the easy linear equation of the past, SDRs need to focus on quality and how to stick out of the crowd if they want to be successful.

Personalizing to Individuals is Challenging at Scale

Personalization is hard and doing it at scale is nearly impossible.

The extra effort required for personalization and the lower outreach volume pushes many organizations to “cheat the system” by mass emailing with light personalization.

While this might bump conversions compared to generic templates, this method of personalizing at a massive scale is unsustainable and hard to make repeatedly successful.

Automation is ineffective because you aren’t being relevant to the recipient. Even if you use personalization that catches attention, buyers won’t act if it’s not relevant.

Organizations struggle to know how to effectively personalize cold messaging, which makes it hard for SDRs to generate consistent results in a repeatable way.

Relevancy Vs. Personalization at Scale

It’s virtually impossible to be personalized and targeted with your messaging while still being able to do it at the scale most sales development teams need.

Instead of trying to be personalized to individuals at a large scale, shift your mindset to being relevant to groups of people at scale.

Relevancy is understanding the challenges, priorities, and needs of your target buyer, rather than trying to find unique personalization about each specific prospect.

If you can identify what a given persona cares about, you can design your cold messaging in a way to capture their attention and add value while still being easy enough to do at scale. 

For example, think about the differences in priorities for a VP of Sales versus a Chief Revenue Officer. If you take note of these differences, you’ll be able to put the most relevant messaging in front of the most relevant person at that target account.

Relevancy at scale is easier to do with automation while still resonating with your prospects, striking an effective balance between high-quality and high-quantity outreach.

Managing Your Outbound Prospecting

Changing environments and evolving strategies require new approaches for managing an outbound sales development program from day-to-day or week-to-week.

SDRs of the past emphasized quantity over quality, so their daily workflow was reflected by the total number of touches they produced.

However, today’s sales development professionals must be more strategic, have a better grasp on time management, and be able to effectively prioritize outbound leads.

Scheduling is Key for SDRs

The best way to keep SDRs consistently hitting quota is to have a solid day-to-day schedule. If reps don’t have a clear path to succeed, they’ll struggle to keep up with the pace of their role.

If an SDR’s schedule is organized, they’re going to have organized results. If their schedule is sporadic or unsupported, reps will struggle to consistently produce results.

As a manager, you should help SDRs understand what they have to do each day to generate positive outcomes and keep them accountable to this system.

Tier Your Outbound Audiences

Every buyer is different and represents a different potential value to your company. SDRs need to be able to recognize this value and balance their time between different audiences.

In such a fast-paced environment, prioritizing accounts is vital for good sales development programs to be effective.

To help prioritize their activities, SDRs should divide their accounts into different tiers based on their value and use a separate outreach strategy for each tier.

For example, tier 1 would be top potential customers. These accounts would deserve the most time, resources, and personalization compared to other tiers. Meanwhile, tier 2 might be a larger group of potential customers that are still valuable enough to invest extra effort.

The value per account decreases for lower tiers, which means segmenting, generic messaging, and sales automation might be necessary to make these accounts worthwhile.

The purpose of tiering is to help SDRs stay organized and ensure they’re spending their time wisely on the most engaged or valuable opportunities. With limited time, reps have to be careful with their time.

Tier Your Outbound Outreach Strategy

Tiering your outbound outreach strategy is important because you want to spend more time personalizing your messaging for the top tier.

Since tier 1 is the most valuable accounts you could close, SDRs should spend more time on research, multi-threaded outreach, personalization, and influencing multiple stakeholders.

For example, Google Alerts can be setup for relevant trigger events on target accounts and LinkedIn can be used to understand organizational structure and develop stronger messaging.

Lower tiers have limitations for how much time and resources can be devoted to each account, so the need for quantity requires persona-based messaging in place of personalization to resonate with groups of people or companies at scale.

By creating unique sales development strategies for each tier, managers provide clear, defined processes that SDRs can repeat to generate opportunities for specific types of buyers.

Outbound Prospecting for Different Business Models

The elements of outbound sales changes depending on the business model. 

The size of your average deal, sales cycles, and your internal sales operations have a major impact on how you should approach an outbound sales development program.

Outreach Changes for Smaller Deal Values

Much of the advice on outbound sales prospecting focus on companies that can afford to invest in sophisticated strategies and techniques to win deals.

However, SDRs that sell smaller deals with larger markets don’t have the same freedom. Certain business models require more sales conversations than large, enterprise deals. 

For example, a transactional SDR selling a $3,000 solution would need to generate 100 deals to generate the same value as a deal coming from enterprise SDR selling a $300,000 solution.

Volume is much more important in this selling environment.

Instead of waiting for triggers, researching personalization, or account-based selling, transactional SDRs are racing to be the first among competitors to reach new qualified buyers.

Because the sales cycle of smaller deals are usually quicker, SDRs don’t have the time to wait for the right opportunities to develop from existing conversations or marketing.

In this selling environment, reps need to be well-versed on industry knowledge, understand how to quickly qualify leads, and have the ability to move a large volume of deals forward.

Time Management for Larger Volumes 

Because smaller deals require a higher volume of conversations, sales leaders need to focus on being strategic with the time their SDRs spend on building pipeline. 

For example, transactional sales development focuses on adding new pipeline. Nurturing one account for months isn’t worth losing out on the countless other opportunities out there.

In addition, SDRs need to be careful how they spend time on research. The more research an SDR does, the fewer total activities and leads they’ll be able to touch every day.

To thrive in an environment with smaller deals, SDRs should be completing more activities, doing less research, and focusing on resonating with personas instead of specific individuals.

The manager’s role is to support the process and empower their SDRs in such a fast-paced, high-volume environment.

With so many activities and conversations, SDRs might need support from managers to help decide when they should make calls, when they should be following up, and how they should structure their daily schedule to consistently hit these higher quotas.

The number one priority of the manager is to make sure everyone’s schedules are aligned with the activities they need to consistently complete to be successful.

Advice for New SDR Managers

Performance falls apart if your SDRs aren’t motivated.

Beyond the skills of outbound sales prospecting, managers need to understand how to manage and motivate the different personalities.

Management strategies continue to evolve and develop nearly as much as the outbound sales prospecting techniques we’ve discussed.

Motivation Depends on the Manager

Every SDR is different so they’ll be motivated in different ways. Ultimately, there are two types of SDR managers, and both can be equally effective in very different ways.

The first is the Rah Rah Manager. They’re all about getting their team fired up and motivated through speeches, mentoring, intuition, or some combination therein. They are the hype man for your SDR team.

The other is the Data-Driven Manager. They empower reps by leveraging performance to show them their best path forward. They are great with reports and data analysis and can relay their findings to the rest of the team in a way that gets them excited to test these new theories.

So what works best for you? Only you can find out. If you’re more Rah Rah and your team doesn’t seem motivated, maybe try mixing in some data-driven motivation and see what happens. 

While you’ll likely be more comfortable with one style over the other, if your reps aren’t showing the drive you know they have, that’s something you have to work on with them while still staying true to yourself and not being something you’re not.

External v.s. Internal Managers

What goes into motivating as a manger is understanding the manager’s perspective of the team and the team’s perspective of the manager.

If you’re deciding between promoting a current SDR and hiring a manager from outside the organization, think about how it would affect the SDRs’ attitudes in each scenario.

If you were an SDR and got promoted to SDR manager, reps might respect you more because they’ve heard you do your calls, send your emails, and use the same process that everyone else is using. 

They will also see a career path they could follow one day, helping you to avoid the constant issue of SDR turnover. 

If you were a manager hired externally it’s a lot harder to acclimate and succeed because SDRs will think they know more than you and that makes for a less effective manager. 

Take into account the amount of training and time it takes to get to know the team, and it’s pretty clear why hiring internally is the preferred route when finding an SDR manager.


Being an SDR isn’t an easy job, and it’s not getting any easier.

Reps have to seriously modernize their outbound prospecting process to keep up with industry changes and buyer behavior. 

More importantly, managers have to empower their reps to make these changes and manage them appropriately as sales development gets faster, harder, and more complex.

Change starts from the top and taking a look at your current outbound process can help illuminate where you can add, improve, and empower your sales development team.

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