Enterprise pedigree
We provide AI and custom software built by the people who did it at Microsoft and Amazon.
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Why LightSight?
Why us
Built for mid-market
Our founders intentionally left enterprise AI to serve the mid-market. Projects are priced and scoped fairly to your business, not a large-cap.
Direct access to AI experts
You work directly with our founders and a team of engineers building your system. Not a bench at a big firm or a single freelancer.
Extension of your team
Our goal is to deliver software tailored to how you work so your systems don't hold you back. If the right answer is an off-the-shelf tool or just a process change, we'll tell you that.
Private Equity Focus
Our products and services are built for private equity funds and their portfolio companies. We understand the constraints and clock you're working against.
Why custom software
AI changed the math on custom software.
Most companies run on off-the-shelf software: subscription-based software that barely differs from one company to the next. It covers about 60% of their workflows. AI now makes it cost-effective to build custom software for the rest.
01
What changed
Since AI has been introduced to software engineering, custom software has become more cost-effective.
Cost to build custom softwareCost of off-the-shelf software
Illustrative. Shows the direction of change, not measured costs.
02
Off-the-shelf vs. custom
Off-the-shelf software means bending your workflows to the software. Custom software is shaped around you.
Off-the-shelf Software
Custom Software
Fit
Off-the-shelf SoftwareYour team adapts to the software
Custom SoftwareThe software adapts to your team
Feature requests
Off-the-shelf SoftwareOn the vendor's roadmap
Custom SoftwareOn your schedule
Upkeep
Off-the-shelf SoftwareThe vendor handles updates and security
Custom SoftwareLightSight maintains it, or hands it to your team
Cost over time
Off-the-shelf SoftwarePer-seat fees grow with headcount
Custom SoftwareYou pay to build once, with no per-seat fees
Differentiation
Off-the-shelf SoftwareStandard workflows shared across your competitors
Custom SoftwareCustom workflows that help your operations become a point of differentiation
At exit
Off-the-shelf SoftwareA subscription the buyer inherits as an ongoing cost
Custom SoftwareAn asset the company owns, which strengthens the exit story
03
Workflows covered
Off-the-shelf software covers about 60% of your workflow needs. The other 40% is manual work.
Off-the-shelf
Built for everyone
~60%of workflows covered
40%manual workarounds
Where the 40% goes:Extra toolsRe-keyed dataEmail handoffsExtra headcount
Custom
Built for you, by LightSight
Built around how you work, so no workarounds
~60% coverage: Gartner
Stop settling for 60%
Book a consultationWhy now?
Where AI breaks, and what LightSight offers
AI stalls at funds and portcos alike due to years of SaaS configurations and manual workarounds, as well as lack of aligned AI strategy.
Where AI breaks
At the fund
At the portco
What LightSight offers
No one to build it
At the fundDeal teams already at capacity. Builds become a full-time job.
At the portcoPortcos told to "implement AI" with no AI leader on the team and limited IT presence.
What LightSight offersEmbedded engineers and AI advisors to develop your product alongside your team.
Security and scalability prevents rollout
At the fund and the portcoPilots work locally; rollout stalls on security, scalability, and stability.
What LightSight offersMission critical, scalable software built in accordance with your fund's compliance needs.
Everything in silos
At the fundFragmented sources make integration difficult and costly.
At the portcoFailed ERP integrations and procurement create fragile and manual workarounds.
What LightSight offersOne pane of glass across teams and processes, built on top of aggregated, clean data.
Adoption not standardized
At the fund and the portcoAI adoption treated as "the wild west": workflows are built and solutions procured one at a time by different users and teams, making governance and centralization increasingly difficult.
What LightSight offersFewer solutions, more users, not gated by per-seat licensing.
Bespoke AI software and expertise tailored to the needs of funds and portcos
How we compare
LightSight vs. others
LightSight differentiates from other AI providers through its enterprise experience, mid-market PE focus, and partnership approach to solving problems.
Built for PE
Full development
Scoped and priced for mid-market
The knock
Large consultancy
Built for PE
Full dev
Mid-market
The knockBuilt for enterprise portcos; mid-market gets enterprise method on a shrunken budget.
Freelance / solo CAIO
Built for PE
Full dev
Mid-market
The knockLimited capacity and depth. Limited ability to maintain security, governance, and auditability.
Generalist AI shop
Built for PE
Full dev
Mid-market
The knockBuild capacity but limited PE experience means process, data sources, and portco ERPs are unfamiliar.
AI point product
Built for PE
Full dev
Mid-market
The knockAnother line on the software bill, unable to provide customized solutions. Stuck in configuration.
LightSight
Built for PE
Full dev
Mid-market
Why LightSightScoped to the mid-market and built for the PE funds and portcos operating within it.
AlignmentStrong alignmentPartial alignmentLimited alignmentNo alignment
What we do
Custom tools for the firm, custom AI solutions inside the portco.
Eight services from diligence through exit, each with the problem it solves, how we help, and case studies where we have them.
Who we are
Operators and engineers who have run AI inside large organizations
LightSight is a partner-led AI consulting and engineering firm. The partners built and ran AI, MLOps, and agentic platforms at Microsoft Azure, led an acquired consultancy through integration at Accenture, and have spent the last several years inside private equity portfolio companies in manufacturing, industrial, supply chain, distribution, and finance. We work as a small senior team, we build with your people rather than around them, and we leave systems the company owns.
Value 1
Simplify
We simplify what's complex, communicate plainly, and use only what works. Our systems make the right thing easy and scale with reality.
Value 2
Iterate
We prototype early, learn fast, and treat feedback as a gift. Every action ties to outcomes; we focus where impact is highest and adapt as evidence changes.
Value 3
Co-Create
We build with your people rather than around them, put clients first, and leave capabilities that last. Ethically, always, without letting ego or fear block the right answer.
The team
Chief Executive Officer
Will Callaway
Led Agentic AI for Azure Ops at Microsoft; Data Monetization Strategy Lead for Amazon Alexa.
Experienced product leader across agentic solutions, AI/ML platforms, and leadership advising. He is recognized for building modern products and driving enterprise adoption in B2B and B2C environments. Collaborative and hands-on, he sets realistic goals with executives that align emerging tech to organizational capability, enabling measurable business impact and process automation. At Microsoft, he led Agentic AI in Azure Ops and served as the Agentic AI Learning Champion for the org. Previous roles include Data Monetization Strategy Lead for Amazon Alexa, Lead Technical PM for flagship data science applications and Call Center automation.
Chief AI Officer
Jackson Rudd
AI lead for Azure Operations at Microsoft; server repair agents, sustainability data platforms, lease automation.
Dedicated to designing AI solutions that simplify work so people can focus on the decisions that matter. Former AI lead for Azure Operations with a strong math background and cross-industry experience, he has built solutions ranging from server repair agents that accelerate technician workflows, to sustainability data platforms, to lease automation cutting cycle time by a third. Known for working side-by-side with technicians, engineers, and business leaders, he ensures every AI system is clear, practical, and built for the people who use it.
Chief Technology Officer
Beau Dekker
MLOps Lead and cybersecurity consultant; security testing on Azure core services and GenAI DevOps.
Former MLOps Lead and CyberSecurity Consultant with 10+ years spanning AI/ML infrastructure, DevSecOps, cybersecurity, and enterprise privacy/compliance. Methodical, reliability-focused, and risk-aware, he builds systems that meet stringent regulatory expectations at global scale. He has lead cross-functional security testing and management on Azure core services and GenAI DevOps across enterprise environments. His work required deep alignment with GDPR, EU AI Act, and leading security/privacy standards.
Chairman of the Board
John Rudd
CEO of SolutionsIQ through its acquisition by Accenture; led Ventures & Acquisitions for Accenture North America Technology.
Driven by a commitment to building resilient, high-growth organizations that can thrive in change. Former CEO of SolutionsIQ, where he pioneered Agile practices and led its acquisition by Accenture, later guiding the global integration of Agile at scale. Most recently led Ventures & Acquisitions for Accenture's North America Technology Services Group, helping organizations succeed in dynamic environments by bringing together strong teams and driving transformation.
Chief of Staff
Molly Wilson
8+ years in strategic communications, executive operations, and client partnerships.
People-first leader with 8+ years of professional experience managing strategic communications, executive operations, and client partnerships. Collaborative, detail-oriented, and focused, she bridges the gap between vision and execution, ensuring organizations have the runway to grow effectively. A former educator and non-profit professional, she brings a rare combination of relationship management and strategic planning skills. These strengths now power her work as Chief of Staff at LightSight, where she cultivates client and partner networks and keeps cross-functional initiatives moving with precision and purpose.
Innovation Lead
Jalen Brown
Scaled startups through acquisition into AutoNation and Resource Innovations; founded an AI-powered learning platform.
Focused on bridging the gap between AI ambition and practical application, he helps organizations translate emerging technology into measurable business impact. His experience spans AI/ML product development, data science, go-to-market strategy, and operational delivery, enabling him to move fluidly between executive strategy, technical implementation, and business execution. He helped scale startups through acquisition into AutoNation and Resource Innovations, and founded an AI-powered learning platform. A former Division I athlete at Oregon and Northwestern, he brings a resilient, adaptable approach to high-stakes engagements.
Senior Engineer
Ellie Abbasi
17+ years building enterprise software and modern cloud applications.
Senior Software Engineer with 17+ years of experience building enterprise software and modern cloud applications. She brings deep engineering experience across front-end and full-stack development, focusing on creating intuitive products that make complex workflows easier to scale. At LightSight, she builds AI-powered and agentic solutions that connect intelligent systems with real-world business processes. Practical and user-focused, she enjoys turning emerging technologies into reliable products that deliver measurable value for clients.
Director of Business Development
Will Chaikin
Consultant at Grant Thornton Stax: PE acquisition diligence and portfolio value creation.
Experienced strategist with a focus on helping organizations make better-informed decisions. He helps bridge the gap between finance, code and corporate strategy, giving businesses the clarity to move forward with more confidence. A former consultant for Grant Thornton Stax, he has spent years collaborating with and understanding portfolio companies to strategize and implement value creation initiatives and help PE firms evaluate potential acquisitions. Prior to this, he assessed ongoing sales and marketing initiatives for Fortune 500 companies.
Book a consultation
Tell us where you are in the hold period: diligence on a target, a portfolio company that needs AI leadership, reporting that still runs on spreadsheets, or an exit story that needs evidence. We will come back with relevant examples and a first view on what is worth doing.
Within two weeks of a first call, deal teams and operating partners typically have a prioritized list of use cases, a cost and payback view for each, and a recommended first build the portfolio company will own.
The first conversation is free, and questions at any level are welcome. We reply within one business day.