DraftKings
Current Technology Stack
BrazeSalesforceBoxCloudflareMongoDBOpenAISlackSmartsheetAtlassian+ Dozens more
2025 Revenue
$6.05B
Employees
5,100
US Sportsbook Marketshare
~32%
Behind FanDuel
EBITDA
$122.83M
Section 01
Introduction
Colleen Reilly
Enterprise Sales Executive
4× President’s Club Winner
Proven Seller | Connector | Entrepreneur
Colleen Reilly is a 4x President’s Club Winning enterprise sales executive with a track record of exceeding annual quotas in highly competitive technical SaaS environments. Expert in full-cycle sales, leveraging various sales methodologies to source and close high-value contracts within complex enterprise environments. As a collaborative partner to Solutions Engineering and relevant cross functional teams, Colleen specializes in translating advanced technical product value into measurable strategic business outcomes.
Section 03
DraftKings Target Account Plan
01
Start with trusted relationships
Leverage personal relationships to gain insights about productivity goals, evaluate time wasted on tasks aligned with Glean value propositions, and understand general use of AI at DraftKings.
02
Develop an informed point of view
Use insights from first layer discussions to further develop and inform POV to deliver to the technical buying committee, likely made up of:
Brian Walker
SVP of AI & Operations
LinkedIn
Brian Harris
Chief Information Security Officer
LinkedIn
Zach Maybury
Chief Technology Officer
LinkedInValue Hypothesis
Why DraftKings Needs Glean Right Now
At the 2026 Investor Day, DraftKings CEO Jason Robins stated that AI is a company-wide force multiplier designed to drive product velocity and operational leverage across their flagship super app, DraftKings Sports & Casino.
01
Maximize Engineering Velocity to Scale the “Super App”
The Context
DraftKings unified Sportsbook, iGaming, and Predictions into a single cross-vertical architecture, reporting a 40% YoY productivity improvement and 100% AI-assisted code reviews.
The Glean Value
As engineering expands to integrate multiple microservices, state-by-state regulatory engines, and unified wallet systems, dev teams waste critical hours context-switching across GitHub, Jira, and documentation. Glean provides unified, permission-aware enterprise search and developer assistance across internal repositories and technical specs, helping engineers build and ship cross-vertical features without re-inventing existing code or hunting for architecture schemas.
02
Elevate CX Containment and Resolve Escalations Faster
The Context
DraftKings highlighted 25% containment on AI chatbot customer service interactions as part of its initiative to roll out AI-driven customer experience enhancements.
The Glean Value
For the remaining 75% of customer interactions that require human support—often involving nuanced issues like payouts, localized betting rules, promotions, or verification—Tier 1 and Tier 2 support agents need instant answers. Glean acts as an intelligent internal coworker, indexing resolution runbooks, Confluence pages, CRM history, and compliance policies so agents can resolve customer inquiries in seconds, directly compounding DraftKings’ customer service leverage.
03
Streamline Multi-State Regulatory and Compliance Overheads
The Context
Consolidating products across 29+ jurisdictions means maintaining dozens of distinct state regulations, responsible gaming limits, and product restrictions simultaneously.
The Glean Value
Fragmented legal and compliance guidelines create bottlenecks for product, marketing, and operations teams attempting to launch localized campaigns and prompt-based merchandising. Glean unifies compliance memos, regulatory requirements, and historical audit documentation into an easily searchable knowledge graph, ensuring go-to-market and trading teams execute rapidly while adhering strictly to jurisdiction-specific rules.
Section 04
Prospecting
For tier-1 target accounts and senior enterprise executives (SVPs, EVPs, and C-Suite), the 2026 data shows that high-volume, automated SDR blitzes (15+ generic touches) trigger spam filters and damage executive credibility. Instead, high-yield enterprise cadences rely on signal-stacking, asynchronous multi-channel orchestration, and intentional spacing.
For C-Suite and SVP targets, the optimal structure is 7 to 9 high-touch interactions over 18 to 21 business days, moving from public presence to high-leverage physical and multi-media channels.
Channel Strategy Principles for SVPs & C-Suite
Calls & Voicemails
Keep voicemails strictly under 20 seconds. Never pitch on a voicemail; treat it as an audio notification for your email or research.
LinkedIn Connection & InMail/DM
Do not pitch in the connection request. Build familiarity first via interaction with their recent public talks, posts, or company filings.
LinkedIn Voice Note (Mobile App)
Voice notes average higher listen rates than InMail because they cannot be easily automated, creating immediate pattern disruption.
Video Email
Must be under 45 seconds, showing their actual dashboard, investor deck slide, or a tailored workflow—never just a talking head.
Handwritten Note (Direct Mail)
Delivered to their primary office (e.g., DraftKings headquarters on Berkeley St in Boston) paired with an executive insight or briefing doc.
18-Day Executive Prospecting Cadence
| Day | Channel | Execution Objective | Key Tactic / Framing |
|---|---|---|---|
| Day 1 | Direct Phone / Mobile (Morning) | Live conversation attempt | If unanswered, leave no voicemail on Touch 1 to avoid premature categorization. |
| Day 1 | Email #1: The Strategic Hook (Afternoon) | Lead with executive priority (<85 words) | Anchor directly to DraftKings’ stated priorities (e.g., product velocity in the super app, reducing time spent chasing information). Soft ask for perspective. |
| Day 2 | LinkedIn Connection Request | Silent brand & name familiarity | Send with no pitch (or a 1-sentence note referencing their specific quote/talk). |
| Day 4 | Phone Call + 15s Voicemail | Audio proof of human outreach | “Hi [Name], Colleen Reilly. Sent a quick note Tuesday regarding your commentary on internal AI leverage across the sports & casino stack. Dropping a quick visual to your inbox now.” |
| Day 4 | Email #2: Video Teaser | Personalized micro-video (30–45s) | Embed thumbnail showing a concrete solution to their public priority (e.g., cross-tool context search across Jira, Confluence, and GitHub). |
| Day 8 | Handwritten Note + Executive Asset | Physical pattern interrupt | Handwrite a direct note to their Boston office desk referencing the executive goal. Include a short 1-page summary of how peer engineering/operations teams solved that friction. |
| Day 11 | LinkedIn Voice Note | Low-friction, mobile-first touch | 20-second audio note sent via LinkedIn mobile app referencing the mailed note and asking for 10 minutes of their perspective. |
| Day 14 | Phone Call (Direct Line) | Bridge touch | Attempt during typical executive whitespace windows (8:00–8:30 AM or 4:45–5:15 PM local time). If voicemail: refer to the LinkedIn audio note. |
| Day 18 | Email #3: Low-Pressure Sign-Off | Professional release & peer benchmark | Mention that you’ll step back to respect their inbox, leave a clean reference point (e.g., how companies at similar scale manage context switching), and keep the door open for next quarter’s planning. |
Target Contacts @ DraftKings
SVP of AI & Operations (e.g., Brian Walker)
Focus on human productivity bottlenecks, context switching across tech stacks, and eliminating the “80% people friction” of finding internal knowledge.
Engineering & Technology Leadership (CTO / Head of Engineering)
Emphasize developer velocity, AI-assisted code search, onboarding speed, and cross-repo context across the unified Sports & Casino super app.
Customer Operations / VP of CX
Focus on tier-2 escalation speed, agent deflection support, and giving customer support reps instant retrieval into multi-state regulatory rules and payout runbooks.
Two sample emails
To: [Name]
Relationship-led · coffee or Zoom
Hi [Name],
Hope all is well! I’m reaching out to see if I can grab coffee with you this week.
I recently took over DraftKings here at Glean. Seeing leadership highlight AI as a company-wide force multiplier—from engineering velocity to CX leverage—sparked some great ideas. We’re helping teams connect internal knowledge so devs ship faster and support agents resolve escalations in seconds, and I'd love to share a few thoughts tailored to your roadmap.
At the very least, it would be great to catch up. Looks like you're [remote, so I can set up a Zoom / in office, so perhaps we could meet at Blank Street on Causeway]?
To: Brian Walker
Research-led · LinkedIn post reaction
Hi Brian,
In all my research about DraftKings, one of your recent LinkedIn posts stood out to me the most:
Your point that getting value from AI is "80 percent people" and requires solving where teams "spend time chasing information or working around broken processes" is exactly why Glean exists.
Glean connects directly to your existing enterprise stack—giving engineering, CX, and operations teams permission-aware context and autonomous agents so they stop hunting for information across tools and can focus on high-velocity execution.
Are you open to a brief 15-minute conversation next week to share how similar teams are driving measurable operational leverage with Glean?
Section 06
Closed Won
A contract I closed at HubSpot — won head-to-head against two of the largest names in enterprise software.
Closed at HubSpot
TRAFFIX
$1M
Contract
Won against
Process Overview
Section 07
AI Tools Leveraged in Typical Process
Glean
My Knowledge & Competitive Engine
HubSpot AI & Gong
Deal Intelligence & Process Optimization
Lovable
Visual Value Delivery & Mutual Action Plans
Glean, Gemini, Claude, & ChatGPT
Pre-Call Strategy & Narrative Polishing
Section 08