Chalkline

What Chalkline does

Chalkline is a Nashville-based private B2B SaaS company that builds an AI-powered promotions platform purpose-built for land-based casino operators in North America. Founded in 2016, the company targets GMs, Property Presidents, Heads of Marketing, and Heads of Database/CRM at casino properties, addressing a specific gap: casinos run dozens of promotional activations per year but historically walk away with little or no opted-in player contact information. Chalkline's five-product suite — Sports Promotions (free-to-play pick'ems and brackets around live sporting moments), Entertainment Promotions (show and concert engagement), Digital Drawings (compliant mobile sweepstakes replacing paper drop boxes), Analytics & First-Party Data (CRM-ready data pipeline), and AI-Enabled Services (done-with-you re-engagement) — funnels every guest interaction into a single opted-in player database that compounds intelligence campaign over campaign via a "player signal graph." Quantified proof points published on the company website include a 600% lift in omnichannel player spend vs. retail baseline, ~$100 average value per driven visit, and 21x average game plays per engaged guest. Reported customers include Caesars Entertainment, Bally's Corporation, Barstool Sportsbook, Choctaw Casinos, Agua Caliente Casinos, Churchill Downs, and JACK Entertainment.

Chalkline operates a quote-based enterprise sales model with annual contract billing and no public pricing. Go-to-market is direct enterprise field sales, with a consultative "working session" approach that audits the customer's promotional calendar, builds a database-growth model, and ships a live promotion within approximately 4 days — compressing typical casino procurement timelines. Distribution is exclusively direct (no resellers or channel partners), and geographic coverage is presently North America (USA), with no disclosed international operations. Marketing channels are primarily the company website (chalkline.com), earned media in gaming-industry trade publications, and direct outreach to casino decision-makers; the company does not appear to invest heavily in paid digital or self-serve acquisition.

The company has raised approximately $4.0 million in total disclosed funding across a $1.3M seed (November 2018) and a $2.7M Series A (August 2021) led by Parlay Capital Holdings and Patrick Conroy. Headcount is reported in the 11-50 range. Leadership comprises co-founder and CEO Daniel Kustelski alongside co-founder Joe Kustelski. The company is incorporated as Chalkline, Inc. in the United States, remains privately held with no public listing, and shows active operations as of 2026 with no disclosed M&A, restructuring, or follow-on financing events.

Name

Chalkline

Legal name

Chalkline, Inc.

Website

https://chalklinesports.com

Company type

Private

Founded year

2016

Operating status

Operating

Headcount range

11–50 employees

Short description

Chalkline is a Nashville-based B2B SaaS platform that converts casino sports, entertainment, and drawing promotions into an AI-powered, opted-in first-party player database for North American land-based casino operators.

Ownership category

akta.pro rank

Product category

Casino Marketing Software

NAICS

Other Gambling Industries (713290)

SIC

Services-Amusement & Recreation Services (7900)

akta.pro primary industry

Casino Loyalty, CRM & Player Development Operations (MPAEAAAJ)

akta.pro secondary industry

Online Casino Platform Providers (PAM, Wallet, CMS, Back Office) (MPAEABAK)

Keywords

• Casino promotions platform
• Sports betting marketing
• Player engagement software
• Free-to-play games
• First-party data CRM

Headquarters

HQ city

Nashville

HQ country

United States

HQ region

North America

Markets served

GTM type

B2B

Offering type

Software

Cost components

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

Revenue model

1. Promotions Platform Subscription: SaaS platform subscription for casino operators to access Chalkline's promotions engine, analytics, and AI services. Pricing appears quote-based and likely varies by property count and feature tier.
2. Professional Services: Done-with-you marketing services including campaign setup, strategy, and re-engagement program management. Likely bundled or offered as add-on to platform subscription.

Pricing tiers

Go-to-market motion1 record

Distribution channels1 record

Marketing channels3 records

Core offering

Chalkline is an AI-powered promotions platform for land-based casinos that turns every retail activation (sports pick'ems, entertainment contests, digital drawings) into a database-building guest engagement experience. The platform comprises five integrated product lines (Sports Promotions, Entertainment Promotions, Digital Drawings, Analytics & First-Party Data, and AI-Enabled Services) that funnel into a unified opted-in player database with AI personalization, enabling casinos to launch promotions in days without developer involvement and measure ROI in CFO-relevant terms.

Product overview

Chalkline is an AI-powered promotions platform for casinos consisting of five integrated product lines: Sports Promotions (free-to-play pick'ems and brackets), Entertainment Promotions (show and concert engagement), Digital Drawings (mobile sweepstakes replacing paper drop boxes), Analytics & First-Party Data (CRM-ready player data pipeline), and AI-Enabled Services (decayed player re-engagement). All five products funnel into a unified opted-in player database with AI personalization, enabling casinos to turn every promotion into a database-building guest engagement flywheel.

Differentiator

Problem solved

Functional benefit

Products and services

• Sports Promotions
• Entertainment Promotions
• Digital Drawings
• Analytics & First-Party Data
• AI-Enabled Services

Quantifiable outcome

• 600% lift in omnichannel player spend vs. retail baseline when engaged through Chalkline promotions
• +2 more outcomes

Named customers7 records

Segments3 records

Ideal customer profiles2 records

Technology focussed Yes

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

AI capability4 records

Feature6 records

Partnerships

Two partnerships are on record, tiered major.

• Churchill DownsmajorOthersMajor gaming brand partner working with Chalkline. Churchill Downs is a prominent horse racing track and gaming company operating casino and online betting properties.
• JACK EntertainmentmajorOthersGaming brand partner working with Chalkline. JACK Entertainment operates casino properties and entertainment venues.

Scale indicators5 records

Recent moves5 records

Expansion highlights5 records

Direct peers

• OPTX: OPTX is an AI-driven casino intelligence platform that provides player development, CRM, and analytics tools for casino operators. It directly overlaps Chalkline in helping land-based casinos turn data into measurable marketing and player-development outcomes.
• Optimove: Optimove is a CRM and customer-marketing platform with a strong iGaming vertical, focused on retention, segmentation, and AI-driven campaign orchestration for operators. It competes with Chalkline for casino CRM and re-engagement budgets.

Broad incumbents

• Playtech: Playtech is a large, established gambling software provider offering casino platform, CRM, and player-engagement products to operators worldwide. It competes as a broader incumbent that can bundle promotional and CRM capabilities alongside its full PAM stack.
• Sportradar: Sportradar is a global sports data and content provider whose technology powers sportsbook operators and adjacent engagement products. It is a broader incumbent that competes for sports-betting-adjacent promotional and engagement budgets.
• Genius Sports: Genius Sports is a sports data, technology, and media company serving sportsbooks and operators worldwide. It is comparable to Chalkline as a broader incumbent providing engagement-enabling infrastructure around sports content.

Emerging players

• EveryMatrix: EveryMatrix provides an iGaming platform suite (casino, sportsbook, payments, CRM) for operators and is increasingly layering player-engagement and promotional tooling. It overlaps with Chalkline's operator-facing marketing and engagement scope as a platform alternative.
• Pragmatic Solutions: Pragmatic Solutions is an iGaming PAM platform provider offering player account management, CRM, and marketing tools to casino and sportsbook operators. It competes for the same operator wallet share that Chalkline targets with its promotional engine.
• SOFTSWISS: SOFTSWISS provides an iGaming platform with casino, sportsbook, and player-engagement modules for operators. It is comparable to Chalkline as another emerging B2B platform serving operator marketing and retention use cases.
• Skilrock Technologies: Skilrock offers iGaming and lottery technology platforms with CRM, player-engagement, and analytics capabilities for operators. It is comparable to Chalkline as a smaller B2B platform addressing casino and gaming marketing needs.
• BetConstruct: BetConstruct is an iGaming and sportsbook platform provider with CRM, marketing, and player-retention tooling for operators. It overlaps with Chalkline in serving operator-side promotional and engagement requirements.

Market position

Strengths4 records

Weaknesses5 records

Competitive moat5 records

Key risks6 records

Key highlights6 records

Customer concentration

• Xx.com/chalklinesports
• Facebookfacebook.com/ChalklineSports
• LinkedInlinkedin.com/company/chalkline-sports

Revenue estimate

Valuation estimate

Number of profiles

Profiles2 records

Funding overview

Funding rounds2 records

Investors1 record

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 Chalkline