Making an outbound pivot as an org in 2025?

Making an outbound pivot as an org in 2025?

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These are the common mistakes we see at Outbound Squad (this will p*ss some of you off)

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⛔️ Marketing writing cold email messaging in a silo

⛔️ Sales leaders writing cold email messaging in a silo

⛔️ Hiring a third party to come up with cold email messaging in a silo

⛔️ Running training sessions with an enablement team that has never done outbound

⛔️ Rolling out arbitrary (and unrealistic) activity targets

⛔️ Not parting ways with reps who don’t outbound (if they’re not hitting quota)

⛔️ Not investing in a sales engagement platform (for AEs too)

⛔️ Not investing in good data (emails and phone numbers)

⛔️ Not prioritizing your top industry verticals and personas

⛔️ Not capturing what good looks like in a simple playbook

⛔️ Not recording cold calls

⛔️ Not expecting reps to pick up the phone and make calls

⛔️ Front-line leaders not “getting in the pit” with reps and making calls

⛔️ Not talking about outbound in every 1on1

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What to do instead:

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✅ Collaborate

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Run messaging workshops with top reps, sales leaders, and marketing TOGETHER. Get a baseline messaging foundation to bring to the rest of the org and ask for their feedback. Adoption is way higher when reps contribute to what they’re being asked to use.

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✅ Standardize a common process

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As soon as outbound starts to work, capture what good looks like. Build a library of successful emails, LinkedIn messages, and cold call recordings.

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And let's stop arguing about scripts. They work. You need to build them. And reps need to follow them.

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✅ Invest in a lean tech stack

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Sales engagement platform (for both SDRs & AEs) and great data are a must. Dialers are a big help as well. Orum 🥇 is my favorite (also a sponsor).

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✅ Weekly enablement sessions

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Sales enablement facilitates these sessions. They do not run them unless they are actively doing outbound. Highlight reps who are making it work.

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✅ Rub shoulders and get in the pit with your reps

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Every front-line leader makes calls alongside their reps each week. Bonus: Sales execs make calls for 1-2 hours every month to show they’re willing to do what they’re asking the entire sales org. to do.

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✅ Senior leaders hold managers accountable

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This has to be a weekly habit for every manager to bring up in their 1on1s. Senior leaders need to talk about outbound in every 1on1, all-hands call, monthly review, QBR, etc

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Going outbound for the first time is no simple task.

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Run through the steps above and dramatically increase your chances of success.

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