TripleSession

What TripleSession does

TripleSession, Inc. is a private Boston-area software company that operates an AI-powered sales enablement platform targeting small and mid-market revenue teams. Founded in 2020, the company sells a per-seat SaaS product that combines conversation intelligence (automated call scoring against customer-specific playbooks), a CRM-synced deal review interface, and a gamified sales training academy with 500+ video courses. The platform's architecture is built on top of the OpenAI API for natural language understanding of sales calls, with native integrations to HubSpot, Salesforce, Zoom, Google Meet, Microsoft Teams, Aircall, and Kixie, plus Zapier connectivity to 5,000+ downstream applications. AI capabilities include automated scoring against custom scorecards, an Ask AI Coach natural language interface, Global Insights synthesis across call corpora, AI Roleplay with dynamic buyer personas, and Moments for auto-clipped best-practice video capture. The company also publishes in 99+ languages.

The company generates revenue primarily through per-seat annual subscriptions across four tiers: Academy Pro ($540/user/year), AI Coach ($660/user/year), the combined Academy Pro + AI Coach full platform ($1,140/user/year), and a custom-priced Enterprise tier with SSO and dedicated support. It also collects one-time concierge onboarding fees of $3,000 (standard) or $5,000 (advanced with roleplay setup), where TripleSession's enablement team builds custom playbooks and calibrates the AI to each customer's sales methodology. Distribution is hybrid: a sales-led motion with direct demo booking and executive outreach, a self-serve free tier for product-led top-of-funnel growth, and a reseller program targeting HubSpot and Salesforce implementation partners. TripleSession has raised $2M in seed funding (January 2023, led by DGF) and holds SOC 2 Type II certification. Named customers include HubSpot, Customer.io, Apollo Insurance, Ignite Reading, Onfly, The Service Center, Trellis, FullFunnel, and Revenue.io, spanning SMB through mid-market segments.

Name

TripleSession

Legal name

TripleSession, Inc.

Website

https://triplesession.com

Company type

Private

Founded year

2020

Operating status

Operating

Headcount range

11–50 employees

Short description

TripleSession is an AI-powered sales enablement platform that combines conversation intelligence, custom playbook scoring, and a gamified training academy for small and mid-market revenue teams, integrating natively with HubSpot, Salesforce, and major meeting platforms.

Ownership category

akta.pro rank

Product category

Sales Enablement Software

NAICS

Professional and Management Development Training (61143)

SIC

Services-Prepackaged Software (7372)

akta.pro industry

PRIMARYEDABABAJ

Sales Operations, Process & CRM (Pipeline/Forecasting)

Education/Corporate Training & Professional Development/Sales & Customer Success Training

SECONDARYEDAFAJAJ

Digital Twins & Scenario-Based Systems Training (Equipment/Process Simulators)

Education/Education Technology (EdTech) & Digital Learning/AR/VR/XR, Simulations & Immersive Learning

Keywords

• Sales enablement software
• AI sales coaching
• Conversation intelligence
• Sales training platform
• Revenue enablement

Headquarters

HQ city

Boston

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2B

Offering type

Software

Cost components

Personnel, Technology or R&D, Marketing or Sales, Infrastructure, Operations

Revenue model

1. Subscription SaaS - Academy Pro Plan: Annual subscription access to gamified sales training academy with unlimited content access, course certifications, gamification features, team course builder, and team training analytics. Billed at $45/user/month ($540/user/year) with annual payment required.
2. Subscription SaaS - AI Coach Plan: Annual subscription for AI-powered call review and coaching including call scoring, custom scorecards, AI coaching, deal insights, Global Insights, CRM autofill, Ask AI Coach, follow-up emails, Moments & Playlists, automated workflows, analytics, recording bot, and call recording integration. Billed at $55/user/month ($660/user/year).
3. Subscription SaaS - Academy Pro + AI Coach (Full Platform): Combined subscription offering both Academy Pro and AI Coach capabilities including AI Roleplay for rep practice simulations. Most popular tier at $95/user/month ($1,140/user/year).
4. Enterprise Custom Plan: Custom pricing for larger teams with advanced needs including ability to upload custom training content, dedicated account manager, expert-led sales workshops, and AI Roleplay. Pricing negotiated based on team size and requirements.
5. Concierge Onboarding Services: One-time professional services for hands-on platform setup including custom scorecard creation, custom AI calibration, automated workflow building, and CRM mapping. Standard tier at $3,000 one-time; Advanced tier including roleplay setup at $5,000 one-time.

Pricing tiers

Go-to-market motion3 records

Distribution channels3 records

Marketing channels5 records

Core offering

TripleSession is an AI Coaching Intelligence Platform for sales teams that automatically analyzes 100% of sales calls against custom playbooks, generates AI-powered coaching insights, and combines them with a gamified sales training academy. The platform scores rep performance using AI trained on each customer's specific sales methodology, auto-updates CRM fields, and offers AI-driven roleplay practice simulations, sold primarily as per-seat annual subscriptions across four tiers (Academy Pro, AI Coach, Academy Pro + AI Coach, and Enterprise).

Product overview

TripleSession is an AI Coaching Intelligence Platform that combines multiple integrated modules for sales coaching, training, and rep productivity. The core platform consists of AI Coach (automated call analysis and coaching), Academy Pro (gamified sales training with 500+ courses), and AI Roleplay (practice simulations with AI personas). These products integrate natively with HubSpot, Salesforce, Zoom, Google Meet, Microsoft Teams, Aircall, Kixie, and Slack via Zapier. The platform is offered in four tiers: Academy Pro ($45/user/month for training only), AI Coach ($55/user/month for call coaching only), Academy Pro + AI Coach ($95/user/month for the full platform), and Enterprise (custom pricing with dedicated account management and SSO).

Differentiator

Problem solved

Functional benefit

Products and services

• AI Coach

Quantifiable outcome

• 6+ hours saved per rep per week through automated call reviews and CRM auto-updates
• +5 more outcomes

Named customers8 records

Segments5 records

Ideal customer profiles1 record

Technology focussed Yes

API detail

Has API

Yes

API docs

API detail

Core technology

AI maturity

App detail

Integration12 records

AI capability10 records

Feature12 records

Partnerships

Ten partnerships are on record, tiered core.

• HubSpotcoreTechnology or IntegrationNative CRM integration partnership. Triple Session automatically updates HubSpot CRM fields after calls with meeting data, deal insights, and next steps. Bidirectional integration allows CRM context to inform coaching insights. Included across all paid plans. Part of the reseller partner program targeting HubSpot implementation partners.
• SalesforcecoreTechnology or IntegrationNative CRM integration partnership. Triple Session pushes call insights, deal data, and coaching recommendations into Salesforce. Included across all paid plans. Part of the reseller partner program targeting Salesforce implementation partners.
• ZoomcoreTechnology or IntegrationVideo conferencing integration for call recording and analysis. Triple Session accesses and processes Zoom cloud recordings and transcripts for AI Coach analysis. Original recordings securely deleted after analysis with encrypted transcripts retained.
• Google MeetcoreTechnology or IntegrationVideo conferencing integration via Google Workspace API. Triple Session accesses and processes Google Meet recordings stored in Google Drive. Integrates with Google Calendar for availability viewing. Compliant with Google's API Services User Data Policy including Limited Use requirements.
• Microsoft TeamscoreTechnology or IntegrationVideo conferencing integration for call recording and transcription. Supports Teams meetings as a recording source for AI Coach analysis.
• AircallcoreTechnology or IntegrationPhone system integration for call recording. Triple Session processes Aircall call recordings for AI analysis and coaching insights. Mentioned in customer logos section.
• KixiecoreTechnology or IntegrationPhone and calling integration for call recording. Triple Session processes Kixie call recordings for AI Coach analysis.
• ZapiercoreTechnology or IntegrationWorkflow automation integration connecting Triple Session to 5,000+ applications. Teams can build event-triggered automations like Slack alerts when calls score below thresholds, or route insights to Power BI, Google Sheets, and custom CRMs via webhooks.
• OpenAIcoreTechnology or IntegrationAI analysis partnership using OpenAI API for analyzing sales calls and providing actionable coaching insights. Data used exclusively for providing personalized insights within user accounts, not for training generalized AI/ML models.
• HubSpot and Salesforce Implementation PartnerscoreChannel Partner/ Reseller/ DistributorReseller partner program targeting CRM implementation partners. Partners refer warm introductions to interested clients, Triple Session runs the sales process from start to finish, partners earn commission on revenue. Program designed for partners with CRM implementation, sales/CS enablement, or revenue operations services targeting inside sales teams.

Scale indicators8 records

Recent moves6 records

Expansion highlights6 records

Direct peers

• Clari: Revenue platform combining conversation intelligence, deal management, and forecasting. Overlaps with TripleSession on call analysis and deal review features, particularly for sales managers who need pipeline visibility — Clari is referenced as a direct alternative on TripleSession's homepage.
• Lessonly (Seismic): Sales training and coaching platform (now part of Seismic Learning) offering interactive lessons, roleplay, and coaching. Direct competitor to TripleSession's Academy Pro and AI Roleplay capabilities within the sales enablement category.
• Allego: Sales learning, coaching, and content management platform with AI-driven call analysis and personalized learning paths. Direct competitor in the AI-augmented sales coaching and training category where TripleSession operates.
• Mindtickle: Sales readiness and enablement platform offering training content, roleplay, certification, and coaching analytics. Closely comparable to TripleSession's Academy Pro plus AI Roleplay offerings, particularly for enterprises formalizing sales training programs.
• Chorus.ai (ZoomInfo): Conversation intelligence platform (now part of ZoomInfo) that records, transcribes, and analyzes sales calls. Competes head-to-head with TripleSession's AI Coach on call scoring, summaries, and coaching, and is the second direct competitor referenced in TripleSession's comparison marketing.
• Gong: Category-leading conversation intelligence platform with AI-powered call analysis, deal insights, and sales coaching. Directly competes with TripleSession in the same mid-market and enterprise sales motion, and is the primary competitor TripleSession explicitly compares against on pricing pages.
• Sales Assembly: B2B sales training and enablement provider referenced on TripleSession's homepage. Competes with TripleSession's Academy Pro on structured sales training, though it is more service-led than platform-led.
• Jiminny: Conversation intelligence and sales coaching platform targeted at SMB and mid-market teams. Directly comparable to TripleSession in price point, customer segment, and feature set, and explicitly listed as a competitor on TripleSession's homepage comparison.

Broad incumbents

• Outreach: Sales engagement platform with a much broader portfolio (sequencing, workflows, Kaia conversation intelligence). Competes with TripleSession on conversation intelligence and coaching but its primary motion is engagement, not enablement.
• Salesloft: Sales engagement platform with Drift-acquired conversation intelligence and deal management features. Comparable to TripleSession on call recording and AI coaching but operates as a broader revenue orchestration suite rather than a focused coaching platform.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks6 records

Key highlights7 records

Customer concentration

Compliance1 record

Revenue estimate

Valuation estimate

Number of profiles

Profiles1 record

Funding overview

Funding rounds2 records

Investors5 records

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about TripleSession