This article was updated on January 5, 2026 with an up-to-date FAQ section.
Businesses communicate digitally these days. And many are struggling to make the transition without experiencing a noticeable dip in conversation quality between rep and prospect. In this post, we asked Jeremy Boudinet of leading sales performance software company, Ambition, to share his top insights on sales communications. The following best practices are taken directly from Ambition clients like ChowNow, FiveStars and Outreach, who use Ambition to track, broadcast, and enhance the quality and quantity of conversations occurring in their front office teams.
In today’s digital era of sales, you must personalize and humanize your sales and marketing communication by automating effectively and tailoring your communication to different business channels.
The emergence of Lead Scoring technology like SalesWings have effectively pulverized one of the biggest obstacles to large-scale sales outreach; first, by auto-ranking your leads based on data-driven metrics that signal the value and attractiveness they represent to you, and second, by automating the steps it takes to set up and run an effective, segmented, and highly-personalized outreach campaign.
Ironically, if you talk to a lot of modern sales organization on the cutting-edge of today’s technology and outbound processes, targeting isn’t the issue at all. Instead, it’s the core pillar of sales itself that these organizations are struggling with – because once you’ve identified the right accounts to reach out to and who specifically you’ll be targeting in those accounts, you still have to – you know – talk to you.
Or really, get them to talk to you. And the automation age of B2B sales has brought with it a veritable crisis of faith in the ability of tech-driven modern sales teams to reliably perform the most core function of their profession – communicate effectively with prospects. On the heels of two Sales Influencer Series interviews with ace communicators Tucker Max and Dallas Hogensen, I’m delivering three of their best practices that cut through the online clutter and get reps communicating like awesome sales pros as opposed to Awesome-O’s.
Best Practice #1. Treat your correspondents with respect:
Technology is placing an inherent demand on value-driven, relevant correspondence. To ensure your communication reaches recipients on that level, make an effort to maximize personalization and minimize roboticism in digital communication. Personalization brings great results. Nevertheless, resources are limited.
Do: Begin all interactions by seeking to add value.
Examples: 1) “Thanks for attending our webinar. Here’s a new eBook we just released on this subject.” 2) “Just shared your company’s new feature in Business Insider. Congrats! Here’s how we help your competitor/peer.”
Don’t: Send annoying emails that have no purpose.
Examples: 1) Touching base. 2) Eaten by alligators?
Best Practice #2. Be timely and part of the conversation.
Go to the places where people discuss topics relevant to your value propositions. Immerse yourself in the community and gain a keen feel for the pulse, resonant topics, and most pressing issues relevant to both your business and community membership.
Do: Adopt research tools to offer timely insight on a topic relevant to them.
Examples: 1) Use Clearbit to find and engage social media profiles. 2) Use Owler to reference timely news article about company.
Don’t: Be a stalker.
Examples: 1) “I see you attended a Big 10 school and minored in journalism. So did I!”
Best Practice #3. Use appropriate channels for communication:
Social media and social prospecting tools like the SalesWing LinkedIn tracking, messaging apps (ex. Slack), and sales, marketing and customer success platforms are offering immediate insights on prospect/client behavior. They also provide a much more informal, direct communication experience that lends itself to personalized conversation.
Do: Commit to finding and infiltrating the right digital communities.
Examples: 1) Engage in LinkedIn group conversations. 2) Join industry Slack channels and online forums (ex. Marketing: GrowthHackers and Inbound.org).
Don’t: Over-automate social media.
Examples: 1) 10 impersonal company LinkedIn updates per day. 2) 10 people from your company tweeting the exact same thing, at the exact same time..
The Importance of Strong Sales-Marketing Communication
The impetus of personalized, business communication is fast emerging thanks to changing workplace demographics and new communication channels. From a demographics standpoint, millennials – the kids who grew up on AIM, Text and Facebook messaging, are now the largest sector of the workplace.
Get used to the new status quo, because it’s not changing anytime soon and team communication effectiveness will be a pivotal point-of-separation between competing B2B sales organizations for the foreseeable future.
Frequently Asked Questions
- For B2B sales reps
- For B2B sales leaders
For sales reps
How do I sound less robotic?
Lead with earned relevance: reference a real trigger, state a clear purpose, and propose one easy next step.
Personalize the first 20–40 words with a buyer-centric observation (recent news, product usage, or content consumed), then connect that to a problem you can actually solve. Ideally you should strip filler like “hope you’re well,” write at an eighth-grade level, and read your message aloud to catch stiffness. Close with a specific, low-effort ask.
Tip: Save three “value-first” openers per persona in your snippets library.
How do I follow up respectfully?
Follow up with new value, not pressure: add a resource, a concise answer, or a relevant proof point.
Space touches sensibly, acknowledge their workload, and give an easy out to reduce friction. By rotating mediums, you’ll avoid repeating the same ask in the same place. Keep subject lines specific and helpful, then close with a single, binary next step (yes/no time or a link to confirm).
Tip: Borrow closing-time tactics that focus on clarity and value.
How do I handle rejection online?
Treat rejection as data and manage the emotional cycle so you can respond professionally and stay productive.
Pause before replying, re-read their objection, and decide whether to ask a clarifying question, offer an alternative, or gracefully close the loop. You can protect your mindset with short resets between sequences and keep a few pre-written, empathetic replies ready for common scenarios. Log the reason so your next outreach improves.
Tip: Build a personal playbook for tough moments.
What’s the right multi-channel mix?
Start with email, phone, and LinkedIn, then layer a second social or event touch if response lags.
Use email for context, phone for fast qualification, and LinkedIn for lightweight social proof. If you’re not getting replies, swap the order or change the medium (such as phone first for operations leaders). Cap daily touches to avoid fatigue and use short voice mails to reinforce value without asking for a callback.
Tip: Plan your week by channel to maintain momentum.
How do I use buyer signals?
Tie your outreach to observable intent (content views, site visits, product activity, or news) and reference that signal in the first line.
Prioritize accounts showing multiple signals within a short window and tailor your point to the exact asset or event. For weak signals, you could ask a question to confirm priority before pitching; for strong signals, suggest a brief, specific next step tied to the behavior.
Tip: Keep a “signal → opener → CTA” cheat sheet on your desk.
When should I switch channels?
Switch channels when intent is high but response is low, or when your message needs richer context than text provides.
After two emails without engagement, try a call or LinkedIn note referencing your original value. If calls go to voicemail, leave a crisp benefit and follow with an email that repeats the point in writing. Move to live conversation when nuance matters: pricing, security, or integration details.
Tip: Keep a two-step fallback ready for every stage.
For B2B sales leaders
What standards should our team follow?
Set clear message standards that prioritize relevance, personalization, and channel fit so buyers receive timely value rather than generic outreach.
Relevance is paramount; 61% of sales leaders prefer a rep-free buying experience. Therefore, it’s crucial to create a concise playbook covering tone, first-line personalization rules, purpose-driven CTAs, and when to escalate from email to live conversation. Include channel guardrails (cadence limits, quiet hours) and examples of good vs. bad messages to reduce variability. You shoul revisit quarterly with win/loss insights and recorded-call snippets to keep the guidance practical.
Tip: Add a one-page checklist reps must run before sending any sequence.
How do I measure conversation quality?
Combine outcome metrics with behavioral signals to score message quality and coach to specific, improvable moments.
Track reply rate, positive outcome rate, meeting conversion, and time-to-first-response alongside behavioral indicators like purpose clarity in the first line, degree of personalization, and channel appropriateness. 10% of weekly messages can be sampled for a light QA rubric and shared anonymized “before/after” examples allow for concrete feedback.
Tip: Publish a simple “quality dashboard” that pairs numbers with two annotated message examples per rep.
Where should we invest in automation?
Automate repeatable logistics (timing, routing, enrichment, and reminders) while keeping first messages and key follow-ups human-written.
Automation can be used to trigger outreach from real buyer intent (form fills, usage milestones, event attendance), enrich accounts, and space touches across channels. Preserve human ownership for discovery invites, objection responses, and late-stage nudges. This hybrid approach scales volume without sacrificing empathy or context.
Tip: Audit one workflow per quarter and remove one step that doesn’t add value.
How many channels are optimal?
Plan for true omnichannel: email, phone, LinkedIn, events, and product-led signals, then test your mix per segment.
High-performing teams meet buyers where they prefer to engage and orchestrate touches rather than over-weighting any single channel. You can define a maximum of two touches per day across channels, rotate media to prevent fatigue, and map channel choice to buyer stage and role. Review cohort performance monthly and prune low-yield steps.
Tip: Start with three channels and expand only when each adds incremental lift.
How do we coach reps humanly?
Coach for intent, not just wording: clarify the “why,” then refine the “how” with concise examples and quick practice.
In weekly sessions, pick one message per rep, restate the buyer’s context, and ask the rep to rewrite the first 60 words to add value. Focus on empathy, purpose, and a single next step, then role-play live to harden the change. Top-performing sales teams keep a library of “golden first lines” by persona so improvements persist.
Tip: End each coaching with a 30-second talk track the rep can immediately ship.
How do we align with marketing?
Share one messaging spine across teams and adapt the surface layer by channel, segment, and buying stage.
Marketing is disconnected from sales more than ever. Build quarterly “message packs” that include the narrative, proof points, objections, and CTAs, then localize examples for top industries. Instrument UTMs and reply reasons so both teams see which angles pull buyers forward. In an optimal scenario, you should hold a monthly 30-minute “message stand-up” to retire weak plays and promote strong ones.
Tip: Co-own a single multi-channel prospecting sequence per ICP and review outcomes together.
Jeremy Boudinet is the Director of Marketing for Ambition, Chapter President for AA-ISP Tennessee and host of acclaimed podcast, The Sales Influencer Series. Contact him via email and learn more about Ambition on our AppExchange listing and G2Crowd page.
Great article, thanks for sharing your insights Jeremy!