Client engagement strategies: How to win more deals

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    Key Takeaways

    • Successful client engagement today requires everyone in go-to-market (GTM) to work from the same source of truth—connecting content, data, and guidance so sellers execute consistently and with confidence.
    • By leveraging valuable insights from their data analytics tied to recent and active opportunities, GTM teams can adjust their approach to ensure reps build meaningful relationships with prospects and drive results.
    • Engaging prospective customers across multiple channels and tailoring messaging, content, and plays to their pain points enables B2B sellers to stand out from the noise, increase trust, and accelerate deal momentum.
    Free Resource
    Guide: What Good Client Engagement Looks Like 

    Client engagement feels easy when the market is strong or your product is the latest must-have. But when conditions are average (and most of the time they are) or less-than-ideal, customer engagement becomes far more fragile.

    You can’t always rely on hype, incentives, or shortcuts.

    Instead, the engagement process often breaks down in quiet, everyday ways, such as a missed deadline, a delayed response to a prospect’s question, an outdated page on your website, or a minor inconsistency that erodes confidence.

    What makes client engagement so hard today is you rarely know which moment will matter most. Different prospects notice different things. Small lapses can shape how leads perceive your reliability, credibility, trustworthiness, and intent.

    Those perceptions—and your ability to provide personalized experiences via bespoke engagement campaigns geared toward potential-client needs—directly influence whether a customer relationship moves forward or stalls completely.

    That’s why effective client engagement isn’t about doing more.

    Rather, it’s about being deliberate and responsive to how target customers behave and what key purchasing decision-makers expect across their respective B2B buying journeys, especially when there’s no external momentum on your side.

    How to build a successful client engagement strategy: A B2B GTM framework

    Successful client engagement starts with sales, marketing, and customer success aligning around shared customer data and real customer behaviors.

    Rather than simply increasing outreach volume, your team will engage customers based on their needs, activity, and stage in the customer lifecycle.

    An effective engagement approach anticipates client needs and questions, and aligns personalized client interactions with real customer behavior and expectations.

    By delivering value when customers expect it, client relationships, client satisfaction, and overall sales success improve without overbearing, unnecessary communication.

    Implement an AI-powered revenue enablement platform to support smarter engagement

    Using an AI-powered revenue enablement platform, you can connect customer data from across your GTM tech ecosystem—including buyer engagement history, purchase history, and deal patterns from your core customer engagement platforms—to surface the most relevant insights before each interaction.

    For example, you can stop relying on memory or last-minute research. Using AI, you can see which content a customer engaged with, what questions typically arise at this stage, and where similar deals tend to slow down.

    That kind of AI-supported preparation allows every sales rep on your team to focus conversations on what matters most to the prospect in that moment.

    Map out the entire client journey to understand where buyers hesitate or need support

    Engagement improves when the entire team understands where customers pause, revisit info, or drop out of the deal altogether. Mapping the customer journey helps identify common friction points across evaluation, decision-making, and post-sale stages.

    When you see where buyers hesitate, such as after demos or before pricing discussions, you can proactively address uncertainty with the right information at the right time. This shifts engagement from reactive to intentional.

    Use defined client engagement metrics that reflect behavior change, not just activity

    Effective client engagement strategies focus on metrics that indicate movement in the sales process, such as repeat interactions, customer success stories, reduced time between milestones, or more complex follow-up questions during evaluation.

    These KPIs, along with ongoing sales optimization, help to determine whether engagement influences decisions rather than simply generating attention.

    Sales performance metrics such as customer effort score, net promoter score, and customer satisfaction score help to evaluate engagement quality. Other customer success KPIs, such as customer retention, customer lifetime value, brand loyalty, and repeat business, indicate long-term impact.

    Client engagement signal to monitorWhat it reveals about client expectations
    Which content stakeholders revisited or shared internallyThey’re re-evaluating alignment across teams. Sharing internally signals internal interest, scrutiny, or comparison—likely weighing business fit, usability, or readiness to take next steps.
    Changes in the types of questions being askedWhen questions shift from tactical to strategic—or vice versa—it shows they’re either narrowing their focus or reconsidering needs. This change often signals evolving priorities or urgency.
    Time gaps between key interactions or milestonesGaps in interactions suggest changing internal priorities or reduced urgency. The deal hasn’t necessarily dropped. Other projects or decisions may be taking precedence before this progresses.
    New stakeholders engaging late in the processLate-stage involvement from new decision-makers usually means a re-review or need for broader alignment. They’re making sure the offering in question fits across different roles before moving forward.
    Repeated focus on implementation, risk, or adoptionOngoing attention to rollout of a new solution details means they’re focused on downstream success. They’re seeking to minimize uncertainty before making a decision with long-term consequences.
    Declining engagement with previously active contentInterest hasn’t vanished. It’s just shifting. Either someone new is leading, or internal focus has moved. Your previous value narrative may need to change a bit to match their new lens or leadership.

    Build outreach around customer needs, not generic sequences

    While personas provide a starting point, real engagement comes from observing existing and new customer behavior. This includes what content buyers return to, which questions repeat across conversations, and where engagement drops off.

    When you ignore these signs and rely only on instinct, the risk of disengagement is high. In fact, 73% of buyers actively avoid suppliers that send irrelevant outreach, per Gartner, making applicability a requirement rather than a nice-to-have.

    For example, technical stakeholders often spend time reviewing integration documentation while economic buyers focus on ROI summaries and implementation timelines. Treating both target audiences the same will almost always lead to someone disengaging.

    A customer-centric approach adapts to these differences, and conversations move faster because each interaction addresses the buyer’s actual concern rather than your assumptions.

    Create GTM feedback loops to refine your engagement over time

    You can increase customer engagement by learning from every interaction.

    Feedback loops capture direct client feedback, customer questions, content usage, objections, and post-sale conversation intelligence. These insights inform future engagement and highlight existing consumer concerns with your company’s offerings.

    By regularly reviewing feedback, you and your team can improve messaging and timing and retire approaches that no longer resonate. Over time, engagement becomes more successful because it adapts to real customer input.

    [Webinar] How digital sales rooms increase client engagement for B2B sellers

    Engage potential customers through the right channels and at the right times

    Customers interact across email, meetings, digital content, and social media channels, but different matters at different stages of the buyer’s journey, and every buyer shops differently.

    This shift highlights why your timing and approach matters more than the number of channels you use. Early, proactive engagement often works best through self-guided digital experiences, while later stages benefit from thoughtful, human conversations that offer greater reassurance.

    Design engagement programs that scale across inside and field sales teams

    Sustainable engagement cannot depend on individual habits or standout performers. Without shared standards, engagement varies across teams, leading to inconsistent customer experiences and unpredictable outcomes.

    “Improvement isn’t simply about tweaking your plan design,” KPMG recently wrote for Harvard Business Review. “It requires realigning sales performance, including territories and quotas.” The same principle applies to client engagement.

    Business growth requires structural alignment, not just good intentions.

    For example, organizations that standardize how teams prepare for customer interactions using shared data and approved content create a consistent baseline experience that leads to mutually beneficial relationships.

    From there, sellers can tailor conversations to the customer’s industry, role, and recent activity. This balance of consistency and flexibility allows engagement to scale while remaining relevant over time.

    The 5-step client engagement strategy blueprint for GTM business success

    Effective customer engagement strategies are intentional. They require discipline in when to engage, what to say, and how to adapt based on real interactions. This five-step blueprint can ensure your sales professionals have meaningful interactions with buying committee members that support their decision-making.

    Step #1: Ditch the monologue, and start listening actively to the prospect’s pain points

    Active listening means understanding customer context beyond what is said in meetings. It includes noticing which content customers revisit, where conversations stall, and which questions remain unresolved.

    When this context is missed, discovery becomes superficial.

    Worse, your client engagement loses relevance.

    “When discovery is shallow or rushed, companies routinely miss crucial context: the real problem the customer needs solved, the decision-making structure inside the account, the stakeholder friction that could derail the deal, and the technical limitations that might prevent adoption later,” B2B sales expert Ron Carson recently wrote for Fast Company.

    Before reaching out to leads, review recent interactions and account-based selling data to understand what the customer is trying to accomplish. When engagement starts with listening, conversations feel relevant from the first sales pitch.

    Step #2: Only engage leads when you are bringing value (tied to their needs) to the table

    Avoid reaching out unless you can offer something that helps the buyer move forward.

    Value does not always have to be new info. Sometimes, it may simply mean reframing a problem or clarifying trade-offs the customer hasn’t yet articulated.

    Sharing how similar orgs navigated internal alignment or avoided common implementation risks can be more valuable than sending another feature overview.

    Step #3: Make every single touchpoint personal and tailored to the stakeholders you engage

    Personalized engagement should be systematic. Establish shared standards for how consistent communication works while allowing personalization at the account level.

    For example, you may follow a consistent preparation framework that includes reviewing stakeholder roles, recent engagement patterns, and known deal risks. From there, personalize interactions based on what matters most to each buyer.

    Step #4: Avoid tactical information delivery at all costs—just have human conversations

    As decisions progress, customers need confidence that a solution will work in their environment and deliver the outcomes they are accountable for. Most of the time, repeating product details adds little value unless the potential customer asks explicitly for it.

    What matters instead is reassurance, clarity, and risk reduction.

    Late-stage engagement is most effective when conversations shift from explaining features to addressing practical concerns, such as implementation timelines and long-term adoption. Focusing on how similar organizations approach similar challenges helps buyers assess feasibility and reduce uncertainty.

    When buyer engagement centers on outcomes and real-world considerations, buyers gain confidence at critical decision points and are more likely to move forward without too much hesitation.

    Customer feedback should shape engagement well before a deal closes.

    Capture feedback through questions raised in meetings, recurring objections, content customers share with their team, and insights from customer success chats.

    Reviewing this information regularly helps you identify patterns and make in-the-moment adjustments. When client feedback is treated as an ongoing input rather than a post-sale exercise, engagement becomes more effective over time.

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    Supporting human-led selling with AI-powered client engagement tech

    Client engagement succeeds for go-to-market orgs like yours today when technology and human judgment work together and simplify selling for reps.

    Leveraging automation tools and purpose-built AI for sales teams streamlines account research, surfaces relevant insights lightning-quick, and supports early interactions with prospects, helping you move faster and stay informed.

    Just don’t forget the ‘operators’ required to wield these tools. Human interaction becomes increasingly important, the more you make the most of AI today.

    Companies across industries are already responding to this shift by rethinking how their sales teams are structured and supported with emerging tech.

    More to the point, many of these firms are placing greater emphasis on specialized roles that excel at discovery, problem-solving, and guiding complex decisions, while investing more deeply in training, preparation, and interpersonal skills.

    With the right tools (read: an agentic GTM platform with AI-powered tools and capabilities for sales, marketing, and enablement) your sellers get the context and insight they need to show up prepared and focused at the moments that matter most.

    Haley Katsman

    As a seasoned Go-To-Market leader, Haley Katsman brings a wealth of experience in building and scaling high-performance teams across Sales, Strategy, Operations, Enablement, and Analytics. She serves as Vice President of Global Strategic Accounts at Highspot and leads the teams driving strategy, revenue growth, and customer experience. Having served as VP of Revenue Strategy, Operations and Enablement at Highspot for 10+ years, Haley specializes in guiding companies through systematic change management, resulting in increased productivity and profitability. Her expertise lies in GTM architecture, driving key GTM initiatives, and advising customers on how to drive behavior change within their customer-facing teams and with buyers, resulting in increased productivity and revenue growth.

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