A Step-by-Step Guide for a Leader to Develop a Digital-First Sales Team

Introduction: Where the Digital Transformation Begins, at the Top

Your buyers are digital. They're checking out on LinkedIn, reading reviews, watching videos, and comparing solutions online. They often may never even talk to a salesperson.

So that brings us to the ultimate question: Has your sales team kept up to reach them where they live?

Building a digital-first sales team isn't about throwing more tools into the mix. It's about leading a cultural shift, where digital engagement becomes second nature and your team learns to influence buyers long before the first meeting is booked.

We’ll take you step-by-step through everything you need to know to make the shift successfully.

Step 1: Redefine What Success Looks Like in a Digital World

The classic sales metrics like calls made, meetings scheduled, or emails sent no longer tell the whole story.

Now, B2B sales success is increasingly tracked by:

Content engagement: Are prospects viewing your demo videos or downloading your guides?

Social activity: Is your team forging relationships and creating conversations on LinkedIn?

Digital touchpoints: How many real engagements are there before a call is even made?

As a leader, your role is to realign what performance means. Identify and reward the behaviors that support how today's buyers want to interact: digitally, asynchronously, and on their terms.

Step 2: Redesign Sales Roles and Skills

Cold-calling ability and charisma are no longer enough to make a top performer. Sellers in the digital-first era require a fresh set of skills.

Key Skills for Today's B2B Sales Professional

Content sharing and curation: Understanding when and how to leverage blog posts, video, and other people's content to inform buyers.

Writing for digital channels: Developing concise, value-based writing for email and LinkedIn.

Master the art of virtual presentations: Speak clearly, use visuals effectively, and keep your message concise on Zoom.

Personalized video messaging: Leverage tools such as Loom or Vidyard to establish a human connection at scale.

Digital empathy: Decoding online behavior and adapting tone, timing, and content in response.

These aren't "nice-to-haves." They're must-haves for establishing trust in a world where interactions take place primarily online.

Step 3: Arm Them with the Proper Tools

Modern sellers need the right digital sales stack to stay competitive. Tools, though, should enable connection, not substitute for it.

Here's what your digital-first tech stack should consist of:

1. Social and outreach tools:

   LinkedIn Sales Navigator

   Salesloft or Outreach

2. Video messaging platforms:

   Vidyard

   Loom

3. Intent and behavior tracking tools:

   Bombora

   6sense

4. CRM and automation:

   HubSpot

   Salesforce

Train along with these tools. Adoption collapses when reps don't understand how a tool aids their process or enables them to close deals quicker.

Competency	Legacy Seller	Digital-First Seller
Primary Outreach	Cold calls, in-person meetings	Personalized video messages, social-media engagement
Content Usage	Company brochures & slide decks	Own and curated blogs, video snippets, infographics
Writing Style	Formal, lengthy proposals	Conversational, concise LinkedIn posts and emails
Presentation Mode	Live demos in boardrooms	Virtual demos—screen share + interactive Q&A
Data & Analytics	Basic CRM activity logging	Real-time behavior tracking (downloads, page views, clicks)
Relationship Building	Rapport via small talk, handshakes	Digital rapport via tailored content and community posts
Tool Proficiency	Phone, email, basic CRM	LinkedIn Sales Navigator, video platforms (Loom, Vidyard)
Adaptability	Follows scripted cadences	Triggers dynamic sequences based on prospect behavior

Maria, an enterprise SDR, noticed low response rates on cold emails.

She recorded a 60-second Loom message addressing the prospect by name, referencing their recent blog post, and inviting them to a brief discussion.

Her personalized video generated a 45% reply rate—3× higher than her email baseline—and booked two discovery calls within one week.

Step 4: Develop a Replicable Digital Sales Process

In order to make digital-first selling scalable, develop systematic workflows that your team can reproduce.

Make use of behavioral data to create trigger-driven cadences. For instance

A prospect downloads a guide, the rep follows up with a video, then a LinkedIn invite, followed by a case study email two days later.

Develop content playbooks aligned with buyer intent. Reps would exactly know what content to use at each stage in the funnel.

Redefine the new sales cycle. It no longer begins with a phone call; it begins the moment a buyer reads your blog or watches a demo.

┌─────────────────────────┐

│ Awareness │ ← Blog posts, paid ads, social shares

│ (100% volume) │

└────────────┬──────────┘

│

┌────────────┴──────────┐

│ Consideration │ ← Video demos, gated guides, webinars

│ (≈60% volume) │

└────────────┬──────────┘

│

┌────────────┴──────────┐

│ Decision │ ← Case studies, ROI calculators, 1:1 videos

│ (≈25% volume) │

└────────────┬──────────┘

│

┌────────────┴──────────┐

│ Retention │ ← Onboarding content, customer success videos

│ (≈10% volume) │

└───────────────────────┘

Step 5: Coordinate Sales and Marketing Around a Common Content Strategy

Sales and marketing can't exist in a silo. In a digital-first model, they are required to collaborate on the customer journey together.

Here's how to do it:

Develop a Service Level Agreement (SLA):

Determine what makes a lead "sales-ready"

Establish follow-up deadlines

Create feedback loops so that sales can drive future content.

Read more on how to maximize your SLA here: Stop Hiding Behind Your SLA: Turn It Into Your Best Sales Tool.

Create a joint content repository: Reps need easy access to blog articles, videos, and case studies aligned with key buyer questions.

Discuss content performance collectively: What is converting? What isn't? Leverage actual data from sales interactions to optimize marketing efforts.

When your sales and marketing teams work together, you don't just create more leads; you close more deals.

Step 6: Train and Reinforce Ongoing

Digital selling is not a single training course. Like any capability, it grows stronger the more you work on it.

Make training part of your culture:

Enhance onboarding by including video presentation basics, LinkedIn content writing, and digital listening skills.

Peer learning: Invite reps to exchange best-performing emails, social posts, or video messages.

Monthly upskilling: Conduct micro-training sessions on content deployment, personalization, or tool use.

Celebrate wins: Acknowledge and reward reps who schedule meetings or close deals through digital-first strategies.

Reinforcement is essential. As cold calling previously needed scripts and training, so does digital interaction.

Conclusion: Your Culture Is Your Digital Strategy

Going digital is not about flipping tools or executing a one-off LinkedIn campaign. It's about reimagining the way your sales team engages, educates, and builds trust in a buyer-driven universe.

You don't need to know everything as a leader, but you must determine the direction.

A digital-first sales team is agile, strategic, and relentlessly focused on the customer. It leans on content to inform, tools to extend, and data to inform every conversation. Above all, it's founded on the principle of continuous learning and alignment.

Take the first step today. Audit your team's digital footprint. What is their LinkedIn activity like? Are they posting value or simply pitching? What tools are they leveraging, and how?

The future of sales is here. It's time to lead the charge.