40+ Hours
Added Weekly
Same Day
Bug Fixes
67%
Lower Costs
Organization Snapshot
Selflessly is an Indianapolis-based corporate giving and volunteering platform. Its mission is to keep workplace-giving technology affordable so more money reaches charitable organizations.
Industry
Technology
Region
Central Indiana
Size
<50 Employees
Development
Internal Build
Deployment
Org-wide usage
THE OPPORTUNITY
Enterprise Expectations. Startup-Sized Resources
Selflessly’s mission is to keep workplace-giving technology affordable so more money reaches charitable organizations. Delivering on that mission requires the Indianapolis company to operate extremely lean, even as enterprise customers expect enterprise-grade support, engineering and compliance.
The company was spending approximately $1,500 each month on contract development, customer-support assistance and financial support, yet important work still slipped through the cracks. Customer commitments could be missed, bug fixes required one to two weeks of scoping and coordination, and enterprise procurement requirements, including security questionnaires and requests for proposals, consumed days of staff time.
In January 2026, an urgent infrastructure-modernization project could not realistically be completed through the company’s traditional contractor model within the required timeline. Selflessly turned to AI for serious engineering work, and it delivered.
The experience prompted a larger question: how much of the company’s operational workload could AI reliably support?
A lean technology company serving enterprise customers needed to deliver more without building an enterprise-sized team.
THE AI SOLUTION
Rather than deploy AI as a standalone experiment, Selflessly built it into both the customer experience and the company’s internal operations. The result is a connected AI system that helps users accomplish more inside the platform while giving Selflessly’s lean team additional capacity behind the scenes.
One AI Strategy, Two Operating Layers
Customer-Facing AI
AI Inside the Selfless Platform
Selflessly developed a custom AI assistant named Phil using the Anthropic API. Integrated throughout the platform, Phil understands each user’s role and workplace-giving program, allowing employees and administrators to accomplish tasks through natural language conversations.
- Answers employee questions using their own giving information
- Finds relevant volunteer opportunities and nonprofit organizations
- Provides personalized nonprofit recommendations
- Approves matching donations according to company policy, with human approval available as a guardrail
- Reviews grant applications and flags exceptions
- Creates campaigns from natural-language instructions
- Drafts thank-you messages and impact reports
- Sends participation reminders to employees
- Answers website questions and qualifies prospective customers
Internal AI
AI Behind the Company
Selflessly also built an internal operating layer using Claude. The system supports administrative coordination, customer communication and software development—giving the company additional capacity without building a much larger team.
- Produces a daily morning brief
- Triages incoming email
- Drafts customer responses for human review
- Maintains a commitments ledger so promises do not get lost
- Identifies and fixes software bugs
- Writes and runs software tests
- Opens pull requests for human review
- Operates an overnight engineering pipeline before employees begin the next workday
RESULTS AND IMPACT
What Changed for the Business
Selflessly’s AI investment did more than reduce expenses. It expanded the capacity of a lean team, accelerated customer response and created capabilities that would ordinarily require additional engineering, support and compliance staff.
More capacity at lower cost
Operating costs for the covered functions declined from approximately $1,500 per month in contractor expenses to approximately $400+ per month for AI tools, while adding an estimated 40-plus hours of weekly capacity.
Faster customer response
Customer-reported bugs can now move from report to deployed fix in the same day, compared with a previous contractor cycle of one to two weeks.
Enterprise capability without enterprise headcount
The lean team can support 74% increase in new deal size since June 2026 while handling product, customer, finance and procurement requirements.
Internal efficiency became customer value
Phil gives employees and administrators immediate, personalized assistance inside the product, reducing support demand while improving the customer experience.
LESSONS LEARNED
Four Rules for Responsible AI Adoption
Guardrails Before Autonomy
Decide what AI may never access or execute independently, and enforce those limits structurally. Selflessly keeps production systems, money movement and sensitive customer communications human-gated.
Document the Business
Give AI access to structured organizational knowledge. Shared memory compounds over time; for Selflessly, a commitments ledger improved customer follow-through more than any single AI feature.
Require Evidence
Plausible answers are not necessarily correct. Selflessly’s most significant AI failures came from agents acting on reasonable-sounding but incorrect assumptions, so important claims require evidence before action.
Treat AI Like a New Employee
Provide context, review early work and expand responsibility gradually. Begin with a repetitive operational bottleneck, not the most impressive-looking demonstration.
Ready to Apply AI to Your Business?
Ready to Partner with INAI? Contact: ai@cicpindiana.com