Adedayo Abeeb
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Adedayo Abeeb
How HighlandX Went from Customer to Investor
A venture firm adopted Raylu to sharpen deal sourcing. The platform outperformed every tool in their stack. Then they led the round.
FIRM HighlandX Series A-C software investing | SPEAKER Michael Lackey Investor | OUTCOME Customer → Lead Investor $8M Series A |
“It’s a game changer. As investors, it’s increasingly hard to cut through the noise - especially in the age of AI, where everything is moving so quickly. Raylu helps surface the details that matter and clearly highlights the key differentiators between companies.” - Michael Lackey, Investor, HighlandX |
BACKGROUND
HighlandX at a Glance
HighlandX, launched by Corey Mulloy and Craig Driscoll, is the next chapter of Highland Capital Partners. The firm targets category-defining software companies, typically at Series A through C - that are often businesses where next-generation players are displacing antiquated incumbents. The firm takes a software and AI-led approach to its workflows and is constantly evaluating data and AI tools to enhance productivity. Michael Lackey, Investor, initially evaluated Raylu as a sourcing tool for the team. What started as a product trial eventually turned into a pre-emptive investment.
THE CHALLENGE
A Sourcing Stack That Couldn’t Match the Mandate
Before Raylu, HighlandX ran a familiar playbook: Grata for sourcing, PitchBook for fundraising data, manual research to develop market maps, and experimentation with LLMs to engineer more efficiency.
For a team focused on identifying the next breakout player in a crowded category, the gaps were costly:
Market maps were too broad. Platforms like Grata grouped companies by surface-level keywords rather than true competitive positioning. For example, IGA vendors would get lumped in with PAM - despite fundamentally different buyers, use cases, and expansion paths. That distinction matters when you're underwriting a specific wedge.
Outreach was a bottleneck. Personalizing a single email - the kind that demonstrates you actually understand a founder’s positioning - meant 15-30 minutes of manual research per company. At volume, this was taking material hours for the investment team daily and weekly.
AI email tools sounded like AI. Every competing solution HighlandX evaluated produced outreach that was obviously machine-generated - generic, buzzword-heavy, easy to delete and therefore incompatible with the firm’s strategy.
LLMs were great at surfacing top industry participants, but lacked the ability to sift through categories to identify companies that match the HighlandX investment mandate, specifically.
“The biggest bottleneck was spending 15–30 minutes on a company’s website just to understand its differentiation and draft an email. Even on a good day, response rates were only around 20%. That process just didn’t scale.” - Michael Lackey, Investor, HighlandX |
THE SOLUTION
What Changed with Raylu
From the first demo, HighlandX saw a platform that didn’t just return lists - it understood how markets are actually structured, accelerating time to expertise and collapsing thesis development cycles.
Market mapping with real precision. Raylu’s maps identify direct competitors at a level of specificity that holds up against industry expert diligence and customer reference calls. With previous tools, HighlandX would run a map, then learn through calls that half the companies weren’t actually competing in the relevant segment. That hasn’t happened with Raylu.
“In the past, you’d do customer reference calls or get into the weeds with industry experts and find out that companies you listed as competitors actually aren’t competitors. That hasn’t been the case at all with Raylu.” - Michael Lackey, Investor, HighlandX |
Outreach that reads like an investor wrote it. Raylu automates the research layer - market positioning, competitive differentiation, company-specific angles - and generates emails that are thesis-driven and sound human. Ali’s background in venture capital and growth equity meant the system was trained on how investors actually communicate, not how generic sales outreach tools think they do.
Immediate adoption, daily usage. The switch from Grata was instant. Today, every member of the HighlandX sourcing team uses Raylu daily. Some run 100% of their workflow through the platform. Others use it for the highest-leverage activities: identifying targets and writing outreach that gets responses.
RESULTS
The Impact
Daily usage Entire sourcing team, every workflow | 15-30 min → minutes Per-company research for personalized outreach |
Deals in pipeline Active opportunities sourced through Raylu maps | Expert-validated accuracy Market maps match diligence findings |
HighlandX now runs a repeatable sourcing loop: establish a thesis, build a market map in Raylu, identify the key players, and reach out with precision. Several companies surfaced through Raylu’s maps are high-conviction targets the team will work to pre-empt before they formally go to market.
THE INVESTMENT
From First Demo to Lead Investor
The shift from customer to investor happened fast. The HighlandX team took a call with Ali and came out a second fast follow-up saying they should seriously look at Raylu as a deal - not just a vendor.
The investment case was straightforward: Raylu sat squarely in HighlandX’s thesis of next-gen software displacing incumbents. Ali had clear founder-market fit having sat in the seat of Raylu’s ICP. The technology was measurably better than anything else available and capable of delivering a return on time immediately.
“When you’re investing in early-stage companies, you’re investing in teams and people. The Raylu team - they’re smart, they’re ambitious, and they’re open to hearing feedback. When you combine those things together, it’s a pretty powerful force. At HighlandX, we say time is one of our most precious resources and this was saving me hours of it while not sacrificing the quality my partnership expects.” - Michael Lackey, Investor, HighlandX |
HighlandX led Raylu’s $8M Series A. The relationship now runs both directions: HighlandX uses the platform daily to source and evaluate deals, and provides hands-on product feedback that Raylu ships against rapidly. It’s a flywheel - the customer makes the product better, and the product makes the customer sharper.
THE TAKEAWAY
The Old Playbook Has a Ceiling
HighlandX was building market maps with tools that couldn’t distinguish between adjacent categories. They were spending 30 minutes per email. They were running reference calls only to learn their competitive landscapes were wrong.
Now they operate a disciplined, thesis-driven sourcing engine - one precise enough that their lead investor saw a company worth backing behind it.
Raylu is how they got there.
See what Raylu can do for your sourcing workflow.
Book a demo at raylu.ai
