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August 5, 2026New
We’ve added 123 sessions to the Triple Session Academy. The library now goes deeper across the conversations that shape the customer journey, from the first outreach and discovery call to negotiation, onboarding, support, and renewal. Alongside deeper coverage of core sales skills, this release adds practical AI for sales workflows, expands customer success and support, and introduces a dedicated insurance collection. The result is a library that better reflects the skills, roles, and markets customer-facing teams work across every day.

Customer success and support (24 sessions)

Support and customer success teams get a broader path from onboarding and adoption through health measurement, renewals, expansion, service recovery, and support operations.

Onboarding and adoption (3)

Design onboarding journeys that move customers from setup to confident product use.

Customer value and health (3)

Measure customer sentiment, health, and retention risk with practical CX and recurring-revenue metrics.

Retention and renewals (2)

Build repeatable customer success routines and manage renewals from preparation through commitment.

Expansion and advocacy (2)

Grow existing accounts through relevant, customer-centered account management and upselling.

Support and service recovery (7)

Help support teams listen, de-escalate, find root causes, and resolve issues effectively.

Customer operations and AI (7)

Improve service infrastructure through ticketing, quality assurance, knowledge management, self-service, and AI-supported practice.

Prospecting (12 sessions)

These sessions help teams build a consistent outbound motion across cold calling, email, LinkedIn, multichannel cadences, and personalized video.

Connecting outbound (5)

Improve cold-call openers, delivery, meeting booking, and voicemail follow-up.

Email prospecting (1)

Protect deliverability by applying practical checks across domains, content, targeting, and sending behavior.

Prospecting for leads (5)

Build repeatable lead-generation and multichannel outreach systems across LinkedIn, email, and phone.

Video prospecting (1)

Use short personalized videos to earn attention and book sales conversations.

AI for sales (11 sessions)

Help your team put AI to work across meeting preparation, lead research, personalized outreach, sales presentations, and revenue analysis.

Meeting preparation and workflow automation (1)

Connect Claude with calendars, Slack, n8n, and other tools to prepare for meetings and enrich leads automatically.

AI prospecting and LinkedIn outreach (6)

Research accounts, generate leads, personalize LinkedIn messages, and build repeatable outbound workflows.

AI-powered presentations (2)

Create sales-ready visual assets and slides faster while keeping room for human judgment and refinement.

Revenue analysis with AI (2)

Use Claude in Excel to build financial models, clean data, automate repetitive work, and surface insights for revenue decisions.

Discovery (36 sessions)

The largest part of the release strengthens question-led selling, from active listening and qualification to urgency and mutually agreed next steps.

Diagnostic strategy (6)

Listen for context, barriers, and underlying needs before moving toward a recommendation.

Discovery questioning (11)

Use probing, consequence, and agenda-setting questions to uncover meaningful business problems.

MEDDICC (4)

Apply MEDDIC and MEDDPICC as practical qualification systems for complex opportunities.

Creating urgency (8)

Connect business impact, cost of inaction, timing, and critical events without manufacturing pressure.

Commitment and next steps (6)

Turn productive conversations into clear commitments, mutual plans, and forward movement.

Segment specialization (1)

Plan territories and prioritize accounts with a deliberate tiering and pipeline strategy.

Presenting and closing (24 sessions)

Move from diagnosis to decision with sessions on value communication, business cases, stakeholder alignment, objections, negotiation, and closing.

Presenting price and value (9)

Quantify outcomes, communicate ROI, and build business cases that stand up to executive review.

Objection handling (9)

Respond to resistance, gatekeepers, price concerns, and delayed decisions while keeping the conversation constructive.

Negotiating and stakeholder alignment (4)

Navigate group buying, technical founders, and multi-stakeholder decisions in enterprise sales.

Winning the business (2)

Bring structured questioning and closing systems together when a qualified opportunity is ready to decide.

Leadership and sales process (2 sessions)

Managers and enablement teams can use these sessions to coach live practice and clarify important steps in the sales process.

Role-play coaching (1)

Use conversation-first role-play to improve listening and rep adaptability.

Sales process (1)

Understand how different proof-of-concept models fit into the path toward a purchase decision.

Psychology of sales (1 session)

A focused session on emotional intelligence reinforces the listening behaviors that support stronger sales and customer conversations.

Emotional intelligence (1)

Practice active listening as a deliberate skill for understanding and responding to others.

Insurance specialization (13 sessions)

The new insurance collection covers prospecting, compliance, referrals, retention, recruiting, Medicare, ACA, final expense, and partner-led growth.

Insurance (13)

Apply sales and customer-management practices in the specific workflows and regulations insurance teams encounter. With this expansion, the Academy covers more of the work customer-facing teams do every day. Practical AI workflows now sit alongside durable conversation skills and role-specific learning, creating a more complete foundation for ongoing team development.