Agents Have Been Making Bad Technology Look Good for a Long Time

Philip Charles-Pierre spent roughly two decades building technology for industries built around agents and intermediaries before ever touching insurance. He started in travel, at a company called Site59, acquired by Travelocity, where he helped build the Travelocity Partner Network. From there he moved to publishing, helping Guideposts modernize during a period of real industry disruption, then into real estate at Smarter Agent, where he and the founding Blumberg brothers built a private-label search and discovery app for large real estate franchises and agents — a genuine counterweight to Trulia and Zillow at the time — eventually sold to Keller Williams. A stint building and selling a background check business followed, before D.E. Shaw and the team that would become Nephila Capital approached him about a technology platform for commercial P&C insurance agents.

What made the insurance opportunity click for him wasn’t a plan to disintermediate agents — it was the opposite. Philip described himself as drawn specifically to hard, B2B businesses that help people who sell to other people do their jobs better, rather than direct-to-consumer plays. Insurance agents, in his framing, are genuine Main Street America business owners — every town has one, alongside a doctor, a lawyer, and a real estate agent — and building real technology for that specific, underserved population struck him as both a meaningfully hard problem and a meaningfully important one.

In Episode 67 of InsurTechTalk, Philip and I covered how Semsee’s name is a literal play on an industry acronym, why he believes insurance actually does a better job than travel or real estate at protecting its own data (even if it’s worse at moving that data efficiently), and why he’d rather partner with best-of-breed vendors than build everything Semsee touches in-house.

About Philip Charles-Pierre

Philip Charles-Pierre is CEO and co-founder of Semsee, a platform helping independent commercial insurance agents classify risk, identify carrier appetite, connect to carriers, and compare quotes — built specifically for the commercial lines segment. Before Semsee, founded in mid-2017, he built agent- and intermediary-facing technology across travel (Site59, acquired by Travelocity), publishing (Guideposts), and real estate (Smarter Agent, acquired by Keller Williams).

The Name: SEMCI, Reworked

Semsee’s name is a direct play on SEMCI — Single Entry, Multiple Carrier Interface, an established industry term for exactly the kind of workflow the company set out to build. Philip’s own account of the naming moment: waking up at 2am and realizing the product was fundamentally “SEMCI-y,” and that swapping the “CI” for “SEE” turned the acronym into a real word that also captured the platform’s ambition — helping agents genuinely see everything relevant to a given risk.

What Semsee Actually Does

Semsee’s core workflow, in Philip’s own framing: help an independent commercial agent classify a risk, identify which carriers have appetite for it, connect directly to those carriers to request quotes, and compare the results — all without re-entering the same underlying information over and over across separate carrier portals. For carriers, Semsee offers the inverse benefit: a platform for understanding where risk is actually coming from and reaching the specific risk they want on demand, rather than relying on the traditional relationship-driven, scattershot approach to sourcing business from agencies (Philip’s own wry example: hoping a carrier rep taking a few agencies out for pizza translates into more submissions).

The Core Pain Point — and What Solving It Unlocks

The foundational problem Semsee set out to solve is specific to commercial lines: agents needing multiple carrier quotes on a single risk in minutes, not hours or days, without re-keying the same submission data separately into each carrier’s own system. Philip was clear that solving this narrow problem well does more than save time — it generates structured data on agent activity that Semsee can feed back to help agents sell more effectively, and it opens a channel for Semsee to work directly with carriers on where their pricing or coverage design might be improved based on real submission-flow patterns. Both effects ultimately serve the more than 31 million small business owners in the US whose commercial coverage runs through this exact agent-carrier workflow.

Agents Have Been Making Bad Technology Look Good

Philip’s sharpest observation about the agent channel specifically: agents have spent years compensating for genuinely poor underlying technology, adapting workflows they’ve run for 5, 10, even 20 years around tools that were never actually built well — and he believes there’s real pent-up demand for technology that simply works and is pleasant to use, even though changing an entrenched workflow is never easy regardless of how much better the new tool is.

He mapped out where agents actually spend technology budget today: agency management systems (AMS) absorb the largest and most consistent share, but agents are increasingly spending on smaller, disconnected point solutions — data and analytics tools, CRMs, VoIP systems — purchased piecemeal to solve narrow slices of a problem, rarely interconnected into one coherent workflow. He added a detail rarely discussed publicly: nearly every agency he visits has built some kind of homegrown workaround — a Google Sheet, a shared doc, an Excel macro — to paper over a gap that purchased technology never actually filled, representing real unmet technology need that doesn’t show up in anyone’s budget line.

On Salesforce’s well-documented push into insurance specifically, Philip was measured: several carriers have built genuinely impressive Salesforce Centers of Excellence, and Salesforce has penetrated the carrier level of the industry remarkably well — but he’s far less certain how much of that investment has meaningfully “percolated down” to reach small agencies, networks, or clusters, which generally lack the budget to license and maintain a Salesforce-scale deployment themselves.

Insurance’s Underrated Advantage: It Actually Owns Its Data

Drawing directly on his prior experience in travel and real estate — both similarly agent- and intermediary-driven industries — Philip made a genuinely interesting comparative observation: insurance, in his assessment, does a better job than those other industries of protecting and retaining ownership of its own data. Where he sees real room for improvement is in getting that data to flow efficiently to where it actually needs to go, when it needs to get there. His framing of Semsee’s longer-term role: as agencies, networks, and carriers get better at actually leveraging their own data, Semsee aims to function as the execution layer that turns that data into better outcomes for the end customer and better economics for the agency — rather than simply another platform holding data hostage in its own silo.

Competing With — or Partnering Around — the AMS Incumbents

Asked directly about Semsee’s relationship to the two dominant agency management system providers in the market, Philip was candid that Semsee doesn’t currently have an official integration with either, despite it being one of the most common questions agents ask. He attributed some of that hesitancy on the incumbents’ side to business model concerns and some to technical friction, but was clear Semsee remains open to deeper integration, arguing that ultimately, data nominally owned by the agent should be able to flow wherever it needs to for the agent to perform better — a dynamic he believes benefits carriers, agents, small business customers, and AMS vendors alike, since agents performing better and generating more revenue means more budget available across the entire technology stack they rely on, AMS platforms included.

He tied this to a broader observation about insurance industry culture he genuinely admires: unlike more purely zero-sum competitive industries, insurance routinely treats a competitor as a potential partner — carriers share risk through reinsurance and Lloyd’s syndicate structures, bundle products across multiple underlying carriers, and pass along business they can’t or won’t retain themselves. He sees that same collaborative instinct extending naturally into insurance technology, not just the underlying risk transfer itself.

The Roadmap: Depth Where It Matters, Partnership Everywhere Else

Asked about Semsee’s future plans, Philip described a deliberately focused strategy: continue building the specific functionality agents are actively asking for to place business faster and more accurately — starting with risk classification and appetite-matching — while explicitly avoiding the temptation to build every adjacent piece of infrastructure in-house. Semsee has no ambition to build its own CRM or its own AMS; instead, the company aims to be genuinely excellent at the specific lead-to-quote-to-bind workflow, partnering with the right data providers, technology vendors, carriers, and AMS platforms wherever that improves the speed and quality of the data flowing into a quote for both agent and carrier.

Traction, Team, and Funding

At the time of recording, Semsee had roughly 1,500 agencies on its platform, working with about 40 carriers, and growing both through direct agency and network adoption and through private-label partnerships. Philip credited that carrier growth specifically to product quality rather than relationship-building alone: Semsee’s bet has been that if agents genuinely love the product, carriers will follow them onto the platform — provided the platform is also structured to make it a more efficient way for carriers to source risk, rather than simply a bait-and-switch built to capture agent attention.

The team stood at roughly 40 people, weighted toward product and technology. Semsee was initially funded by D.E. Shaw and Nephila Capital (since acquired by Markel), and had recently added 01 Advisors — the venture firm founded by former Twitter executives Dick Costolo and Adam Bain — as an investor, alongside a recently closed Series B round (amount undisclosed).

A Detour Into Niche Underwriting: Knockerball

In a lighter aside, Philip mentioned that one of Semsee’s agency partners, based in Connecticut, underwrites a program for Knockerball associations across the country — the bubble-suit sport where participants bounce off each other inside inflatable spheres. His broader point, made half-jokingly but genuinely: if a real activity carries real risk, someone in the insurance industry will eventually figure out how to underwrite it.

A New Category Taking Shape: “Keyboard Interruption”

Recorded roughly 405 days into the Russia-Ukraine war, the conversation turned briefly to a genuinely emerging risk category: startups with concentrated engineering teams in geopolitically or environmentally exposed regions. Philip noted Semsee itself works with a development team based in the Dominican Republic, raising its own version of the same underlying concern — hurricane exposure and power reliability, rather than geopolitical risk specifically — and floated, half-jokingly, a coverage concept for this kind of exposure that doesn’t cleanly fit existing categories like business interruption or supply chain coverage, informally dubbed “keyboard interruption.”

Recommendation: The Obstacle Is the Way

Asked for a closing recommendation, Philip pointed to The Obstacle Is the Way by Ryan Holiday — a book he’d shared with his entire team. With a master’s degree in philosophy of religion and a long-standing interest in Stoicism, he described the book as a genuinely compelling modern take on Stoic philosophy applied to overcoming obstacles directly rather than around them. He added a few lighter, informal picks in passing: the bands Khruangbin and Leon Bridges in music, and Ozark and Ted Lasso in television — describing his own outlook as something of a balance between Ozark’s cold pragmatism and Ted Lasso’s persistent optimism.

Key Takeaways

• Semsee’s name is a direct play on SEMCI (Single Entry, Multiple Carrier Interface), reflecting its core function: letting commercial agents classify a risk, identify carrier appetite, and get comparable quotes without re-entering the same data across multiple carrier systems
• Solving the core speed-and-re-keying problem generates a secondary benefit — structured activity data Semsee can use both to help agents sell more effectively and to give carriers real feedback on pricing and coverage design
• Philip’s assessment that agents have long “made bad technology look good” points to genuine, underserved demand for well-built agent tooling, even though changing entrenched agency workflows remains genuinely difficult regardless of product quality
• Insurance, in Philip’s cross-industry view (drawn from travel and real estate), does a comparatively good job of protecting ownership of its own data — the bigger unsolved problem is making that data flow efficiently to where it’s actually needed
• Semsee deliberately avoids building adjacent infrastructure (CRM, AMS) in-house, focusing instead on being excellent at the lead-to-quote-to-bind workflow specifically and partnering with best-of-breed vendors elsewhere in the stack
• At the time of recording, Semsee had roughly 1,500 agencies and 40 carrier partners on its platform, a team of about 40 people, and had just closed a Series B backed by D.E. Shaw, Nephila Capital (now part of Markel), and 01 Advisors
• Insurance’s cultural norm of competitors partnering with each other (through reinsurance, syndicated risk-sharing, and bundled multi-carrier products) extends naturally, in Philip’s view, into how insurance technology vendors should approach interoperability rather than pure walled-garden competition