Pipeline Generation Sales Management

How We Increased SDR Qualified Opportunities by 92% with Strategic Sequences

With sequences featuring customizable templates, we got our sales development team out there selling (not stuck in spreadsheets). Here’s how we integrated automation without losing personality.

Lauren Wadsworth, VP Global Sales Development, Segment's Avatar

Lauren Wadsworth, VP Global Sales Development, Segment

This article is part of our Outreach on Outreach content series, where we showcase our own revenue team’s use of the Outreach Sales Engagement Platform to help you drive success at your own company. We share workflows and strategies, backed by original research and data from the results of our own experiments and customer base.

Today’s article is a special guest edition from Lauren Wadsworth, Head of Global Sales Development at Segment.io. Her team is in charge of driving pipeline for the company that was recently acquired by Twilio for $3.2B.

Our sales team was hitting a wall.

We knew our sales development team was full of extremely driven reps with winning personalities. And volume was not the problem; we were reaching out to prospects left and right.

But meetings booked were low, and the team was drowning in spreadsheets.

I’m not blaming our SDRs.

The real problem: our messaging orchestration was not built for success or scale.

Each rep created their own messaging sequence for reaching out. The result? Our system had over 5,000 different messages going out to prospects.

What’s worse? Those messages weren’t resonating. We had a high response rate, but it consisted mainly of emails like these:

“Please remove me from your mailing list.”

“Not interested."


“I’m not interested at this time.”

“Unsubscribe please.”

We needed a way to simplify how our sales team reached out to prospects—and we found it with Sequences and Snippets. With a standardized Sequences and Snippets plan, we could make sure reps send the most relevant messaging to their prospects at the right time—without sounding like a robot.

We decided on a four-step game plan:

1. Standardize Messaging: Create messaging templates that allow customization, but are still specific enough to analyze effectively.

2. Nail Down Sequences: Build a series of touchpoints based on buyer personas and customer behavior.

3. Pilot Program: Pick a team of 6 SDRs (“Sales Team 6”) to test the program.

4. Expansion: Roll out the new sequence strategy to the rest of the team.

    The results? We increased the average number of qualified opportunities per SDR by 92% that year.

    Even better? We started getting emails like these:

    Best of all, our reps got out of the spreadsheets and back to what they do best: selling!

    Here’s how we did it.

    Step 1: 'Templatize' Emails to Balance Standardization with SDR Autonomy

    Something in our emails and LinkedIn messages wasn’t clicking. But without standardization, we had no way to measure which content resonated and which...didn’t.

    Creating uniform messages for every touchpoint seemed like an impossible task. Each SDR already had their own emails, phone scripts and LinkedIn messages that they liked to use. The last thing that our team wanted to do was send out a bunch of canned messages with their names on them.

    We were stuck. It was time to call in the experts.

    We tapped RevShoppe, an agency dedicated to sales engagement transformation, to help develop our messaging and sequence strategy inside of Outreach.

    One of their first tips was to use email templates that allowed reps to fill in specific aspects in their own words rather than fully automated emails. 

    We created these templates based on specific sequence stages and buyer persona research (more on that in the next section).

    These templates helped make our outreach personalized and standardized. Our reps loved not having to start from scratch for each email. They follow a messaging strategy that’s already been laid out and tested. But they still have enough wiggle room to write with their own voice.

    We also gave reps the option to insert snippets of pre-written text (e.g. links to relevant case studies) to save even more SDR time. Win-win!

    Step 2: Nail Down Core Sequences with Buyer Personas

    Next, our 5,000 sequences had to go. Our goal instead:

    1. 3-4 core sequences per buyer persona

    2. A sequence for inbound leads

    3. A sequence for informed (marketing-engaged) outbound leads

    We wanted to reach out to our prospects across multiple channels in a way specifically tailored to their buyer persona, without losing scalability.

    Sounds good in theory, right? Here are the rules that we developed with RevShoppe to put these goals into practice inside of Outreach:

    Goal 1: Keep sales outreach cycle organized and efficient

    First Tactic: Limit our sequences to 15-20 steps over 30 days

    Goal 2: Connect over multiple touch points to avoid inbox fatigue

    Second Tactic: Only allow 3 manual emails and 3 LinkedIn touches max

    Goal 3: Tailor the process based on buyer persona’s behaviors

    Third Tactic: Develop 3-4 sequences per persona to test which methods are most effective

    Goal 4: Embrace personal customization without losing scalability

    Fourth Tactic: Lean into customized emails, phone, and video more heavily in the beginning, when we are most likely to connect. Only automate follow-ups, 1-2 nurture emails, and the final break-up/referral email.

    We structured the sequences to have 15-20 steps over 30 days to help keep our sales cycle contained and efficient.

    To avoid overwhelming our prospects’ inboxes, we limited ourselves to a max of 3 manual emails and 3 LinkedIn touches over that time period . We expanded our sequence to include multi-channel touch points that our buyer personas would resonate with. Our SDRs wouldn’t just email prospects, but would send LinkedIn messages, custom videos, and regular old phone calls.

    In order to emphasize personalization in a way that was scalable, we dug deep into our buyer personas. We built 3-4 sequences for each persona specific to their behavior. Multiple sequences allowed us to test our outreach strategy versus making assumptions. For example, our reps had observed that our engineering persona hated telephone calls. We confirmed that hypothesis with data that revealed sequences with fewer phone calls outperformed those with more.

    Finally, we leaned on personalized templates for most steps, with extra customization on early touch points to establish a personal relationship more quickly. The only fully automated emails were follow-ups, 1-2 nurture emails, and the final break-up or referral emails. We generated this strategy based on advice from Sam Nelson, our favorite blue-haired friend who also happens to be an SDR Leader at Outreach.

    Here’s an example of a sequence that we came up with:

    Putting these sequences into practice was easy with Outreach. The software prompts the sales rep each time one of these steps is scheduled to occur. Smart views also allow them to optimize their workflow ahead of time.

    Now, all we needed was to get the team on board!

    Step 3: Encourage Buy-In with a Pilot Program

    Changing our entire outreach process wasn’t going to happen overnight. And shoving a whole new messaging system down the team’s throat guarantees that everyone will hate it.

    Instead, we decided to build out this process with the team. We started a six-week, six-person pilot program—aka “Sales Team 6."

    Our theory? If a few SDRs got results, more would want to know how. Plus, collaborating with reps directly would only improve our sequences.

    Sure, we had a little fun with the name. But making the pilot process fun—naming the group, meeting weekly, highlighting their membership to sales and marketing leadership—helped our reps get invested early on. It also didn’t hurt that the team knew they were shaping the future of SDR strategy at Segment. Plus, who wouldn’t choose a badass nickname over a bureaucratic training program?

    We met for an hour each week for six weeks. Each meeting followed a similar format:

    Feedback: During the first 20 minutes, we took down feedback and made workflow and messaging changes immediately. This step helped encourage buy-in and drove quicker results.

    Highlight Wins: We highlighted any wins and strong template examples. Celebrating success helped boost morale and encouraged the team to adopt tricks from others’ templates. After all, there’s no such thing as plagiarism in sales development!

    Share metrics: Reply rates and meetings should increase substantially (after four weeks, our reply rate jumped from 4% to 16%). But even if the numbers don’t rise right away, your team should focus on transparency.

    Adopting the new sales sequences may not come easy to your pilot program at first. If your reps are used to a high volume of automated/mass blast emails, limiting the amount that they can send will feel frustrating. Outreach will let you set “throttle limits” to ensure that they’re not spamming prospects. Restrict access to previous or automated sequences so they can’t fall back on them when they don’t see immediate results

    Others may struggle with writing custom messages. At first, don’t let them spend more than 20 minutes personalizing one email. Instead, have them start with account research. That way, they can apply it to all the prospects that they reach out to. Then they can focus on specific WOW-factor intro lines for each prospect. After some practice, you want their average personalization time to be 3-5 minutes max.

    As pilot members adapt to the new system, they may experience some growing pains. Restrict access to previous or automated sequences so they can’t fall back on them when they don’t see immediate results. Eventually, they will see positive change. Here’s what our team had to say about the process:

    In addition to the weekly group meetings, individual feedback is crucial. Personalized follow-ups feel uncomfortable at first, and good account research takes time. Your pilot team members will need constant coaching—in person, on the floor, and 1:1 time. Listen to their calls, review every email sent from their new sequences, and provide immediate feedback to set them up to succeed.

    Step 4: Roll Out System (and Additional Sequences) to the Team

    You’ll know quickly if you selected the right SDRs for the pilot: soon, other SDRs on the team will want to get on the new workflow. These reps haven’t had the full training or hands-on coaching yet, but that’s okay. Let them dig in and start using the new sequences for themselves. Ideally, there will already be a soft transition to the new method before a more formal one is applied.

    To make a more formal transition less scary, we recommend that you:

    1. Set up smart views in advance so that SDRs can optimize their workflow ahead of time

    2. Clear out overdue tasks so that the platform isn’t clogged up with old data

    3. Restrict access to any previous or automated sequences so that SDRs adopt the new system and don’t fall back on old habits

    With the right tactics, you can even get the marketing team on board with the process! Each time our marketing team released new collateral, we asked them to create relevant Outreach snippets. That way, our SDRs could incorporate them into their outreach with just a click. (Marketing and sales alignment for the win, right?)

    To make adoption as simple as possible, your first iteration should only have 3-4 core sequences by persona.

    As you grow, you will continue to customize your outreach. For example, three months after our pilot program, we added differentiated sequences by sales segments (enterprise, middle market, and growth). We also built messaging workflows around certain industries, customer journeys, and languages. After a year, we even made separate sequences by region and region-specific delivery schedules.

    Today, our SDRs can use up to 20 sequences to meet their specific scenario. While SDRs can create templates (objection handling, re-engagement, referral, etc), they must be approved by SDR leadership and RevShoppe before being uploaded into Outreach and turned on for the entire team to use.

    This limitation prevents the system from becoming too crowded (see: our original 5,000 sequences problem) and ensures that only the strongest messages are used.

    A New Way to Reach Out

    Yes, sales teams may resist following a sales sequence.

    But having standard templates and schedules actually makes it easier to customize messages for larger groups of prospects. And with sales sequences in place, they can spend less time in spreadsheets and more time selling.

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