Engageware CEO Trigger: Sell AI Agents & Scheduling

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🚀 Battle Card: Engageware

Quick trigger: Dan O’Malley appointed CEO (≈ 2025-09-03)

👤 Decision Maker in the News

Dan O’Malley, Chief Executive Officer · 🔗 LinkedIn

💡 Why It Matters

New leadership with deep financial-services and AI experience will accelerate platform expansion and enterprise adoption → Source

🎯 Core Pain Point

Scaling AI-driven customer engagement across global enterprise clients

Integrating scheduling, knowledge management & AI Agents into existing workflows

💰 What to Pitch

Primary: AI Agents → Automate routine inquiries for 24/7 support efficiency

Expansion: Appointment Scheduling → Cut no-shows and optimize resource utilization

🗺️ Quick Context

HQ: Tewksbury, MA

Employees: ≈ 200

Rev: ≈ $50 M

Website: engageware.com

🤼 Competitive Intel

*Which other vendors you’ll probably face to win Engageware’s business.*

Salesforce Service Cloud — CRM / Customer Support

Unique edge: Deep ecosystem integration
Evaluated by CIO & VP Customer Experience

Zendesk — CX / Support Automation

Unique edge: Rapid deployment & rich app marketplace
Evaluated by Director of Support Operations

Genesys — Omnichannel Engagement

Unique edge: Real-time AI insights across voice & digital
Evaluated by VP Contact Center

LivePerson — Conversational AI

Unique edge: Messaging-first, AI conversational design
Evaluated by Head of Digital Experience

✅ Do-Now Checklist

Connect with Dan O’Malley on LinkedIn (link above)

Reference the Engageware sales trigger in your first email/DM

Highlight AI Agents & scheduling wins in outreach

Schedule next touches in CRM (Day 3 & Day 10)

Next Step

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Keep this Engageware sales trigger top of mind as you work the deal.

🧠 Copy My Prompt for Personalized Cold Outreach

────────────────────────────
✏️ YOUR COMPANY
────────────────────────────
OUR_COMPANY   = ❑<your company>❑
OFFER_BRIEF   = ❑Automate customer engagement with AI Agents & scheduling❑
PROOF_METRIC  = ❑40% faster response times❑
CTA_STYLE     = ❑quick_call❑
TONE          = ❑friendly❑

────────────────────────────
📌 TARGET COMPANY
────────────────────────────
NAME        = Dan
COMPANY     = Engageware
DEPT        = Customer Engagement
SIZE        = 200
BOTTLENECK  = Scaling AI-driven customer engagement
EVENT       = CEO appointment
DETAIL      = appointed CEO to drive platform expansion
PAIN        = Integrating scheduling, knowledge management & AI Agents into existing workflows
SRC         = http://cts.businesswire.com/ct/CT?id=ftfLlWd9aZbF2NXfwppam3Bd664=&newsLang=en&newsId=20250903047953&div=41152219
SIM_CO      = ≈ TBD
WIN_METRIC  = ≈ TBD
NEXT_SIZE   = ≈ TBD
EMP_EST     = ≈ 200
REV_EST     = ≈ 50M

────────────────────────
TASK FOR CHATGPT
────────────────────────
Role: “NewsletterForLeads SDR-Assist”.

Validate any ≈ guesses via SRC.

EMAIL  (keep breaks):
Subject: 200-person Customer Engagement

Dan—noticed your Customer Engagement team is ≈ 200.

That’s when Scaling AI-driven customer engagement slows growth.

We helped ≈ TBD fix this with Automate customer engagement with AI Agents & scheduling.

Result: ≈ TBD.  
Quick call?

PS—next bottleneck hits ≈ TBD.

DM ≤45 words, TONE:
Saw your post about appointed CEO to drive platform expansion — Integrating scheduling, knowledge management & AI Agents into existing workflows.  
Automate customer engagement with AI Agents & scheduling. 40% faster response times. Quick chat?