Winning in Florida government takes more than meetings. Success is built on knowing what the right meeting is -- and what needs to happen before, during, and after it. Whether you are pursuing a government contract, moving legislation, or securing an appropriation, we make sure our clients are at the right door, at the right time, with the right message.
CSG maximizes every client engagement through a comprehensive understanding of Florida's policy, appropriations, and procurement processes -- backed by decades of relationships with the elected officials and professional staff who drive government decisions at every level.
Strategy, advocacy, and execution by one of Florida's top operators
Every client comes to us with a different challenge. Some need to move government, some need to sell to it, and some need both. What they all need is someone who understands Florida's government market from the inside -- the policy, the procurement, the players, and the politics that connect all three.
Whether you are securing an appropriation, passing legislation, killing a bill, or navigating an executive branch outcome, success depends on understanding how Florida government actually works -- not how it is supposed to work. We represent clients before the Florida Legislature and Executive Branch, and coordinate local government advocacy across Florida's cities and counties. State legislative, state executive, and local government representation are available separately so you only pay for what your situation requires.
You are in the market but leaving opportunity on the table. The problem usually is not your product -- it is timing, targeting, and positioning. We use proprietary market intelligence and procurement data to identify where your best opportunities are, who the right contacts are, and what needs to happen before your sales team walks in the door. We specialize in government technology but our platform applies to any industry pursuing Florida state and local government contracts.
Florida's government market has its own rules, relationships, contract vehicles, and procurement rhythms that are not obvious from the outside. We help new market entrants understand where to focus, what contracts they need to be on, which partners and primes to align with, and how to build the relationships that turn into revenue. We compress years of market learning into a structured entry strategy so you are not starting from zero.
Not every company needs ongoing consulting. Some need a starting point. We offer Florida Market Intelligence Reports -- proprietary analyses built on real procurement data, agency activity, and market signals. Whether you are deciding if Florida is worth pursuing or you want to know exactly where your sales team should focus right now, we can deliver an expert assessment of the current opportunity landscape, the agencies sending buying signals, and where we would concentrate if we were in your shoes. Snapshots of a market that moves fast. Ask us about it.
Most consulting firms add technology as an afterthought. We rebuilt ours around it. We built a proprietary intelligence platform specifically for the Florida government market, tracking procurement activity, contract vehicles, agency IT spend, lobbyist registrations, and market signals in real time. In an industry where most firms still run on rolodexes and institutional memory, our clients get intelligence-driven strategy backed by data nobody else has.
Jon Costello began his career in federal acquisition program management on the buyer side, then served as Governor Rick Scott's first Legislative Affairs Director and a senior policy advisor -- one of the most consequential roles in Florida government. Over the past two decades he has represented technology companies, healthcare organizations, professional and business associations, and Florida local governments across every dimension of Florida's legislative, executive, and procurement processes. That depth of experience on every side of a Florida government deal is not something you can replicate. It is built over a career in one market.
The old model -- big firm, big staff, generic advice -- is not what wins in Florida's government market. What wins is distilled knowledge, proprietary intelligence, and relationships built over decades of doing this work at the highest levels. CSG has been operating in this market since 2020 and we have rebuilt around a simple premise: one firm, deep expertise, better outcomes. No firm in Florida combines the government experience, the private sector track record, and the intelligence infrastructure we bring to every engagement.
Jon Costello has navigated Florida's legislative and executive processes at the highest levels -- from managing Governor Scott's legislative agenda to securing critical appropriations and defeating legislation that threatened client interests. Two decades of results in Tallahassee means we know how to count votes, work committees, and move the levers that produce outcomes -- not just relationships.
A selection of the technology firms, national brands, and governments we have worked with over the years, across government affairs, procurement, and SLED sales advisory.
Past and present engagements through Costello Strategy Group and formerly affiliated firms. Not a current client list. See the full work →
Jon Costello has spent his career at the intersection of Florida government and the private sector. He began in federal acquisition program management, learning how government buys from the inside, before transitioning to contract lobbying and government relations work in Florida. He joined the leadership team of Rick Scott's initial successful campaign for Governor in 2010, then served in the Governor's Office as Legislative Affairs Director and senior policy advisor -- one of the most consequential roles in Florida state government.
After leaving the Governor's Office he returned to private practice, spending several years with a traditional law and lobbying firm before founding CSG in 2020 with a different vision -- a tech-driven consultancy built around proprietary market intelligence rather than the rolodex-and-relationships model that defines most of the industry.
Over a career spanning two decades, he has represented technology companies, healthcare organizations, professional and business associations, and local governments of every size -- from Miami-Dade County to the Town of Melbourne Village -- across every dimension of Florida's legislative, executive, and procurement landscape. Twice appointed by Governor Scott to the Northwest Florida Water Management District Board, Jon has maintained an active role in Florida government beyond his client work. He is a Former Adjunct Professor at Florida State University's renowned Masters in Applied American Politics and Policy program, where for more than a decade he taught Political Communications -- a course required of every graduate student in the program -- educating many of the top political operators working in Florida government and politics today.
He also publishes The Costello Brief, a weekly newsletter covering Florida government technology, procurement, and politics, and is co-founder of GovMastery, national SLED advisory and training for companies serious about winning government business.
The Costello Brief is the weekly read for everyone serious about Florida government technology, policy, and procurement. Every week, Jon curates the most important news, intelligence, and market signals -- who moved, what contracts were awarded, and what it means for your business. Free. Weekly. Essential.
Subscribe to The BriefWhether you need to influence policy, secure an appropriation, or win more government contracts, preparation is the difference between activity and outcomes. CSG clients operate within the Florida market with an intelligence advantage only we can provide. Are you ready to pitch less and win more?