Why we're doing this

Ryan Patton is conducting structured competitive reconnaissance across Sarasota, Manatee, and Charlotte counties — both passively (online/LinkedIn) and actively (chamber events, networking). This guide tells him what to look for and why it matters. The capture form at the bottom logs findings per competitor.

Keep the hats separate. When networking at chamber events or business alliances, you are there to build relationships — not visibly audit people. Take mental notes during the event; log them after. Never ask direct questions that telegraph competitive intent (e.g., "what do you charge per seat?"). Good intel comes from listening, not interrogating.
What "oppositional research" actually means for us: We're not trying to copy anyone. We want to understand where competitors are weak, where they're strong, what verticals they've staked out, how they talk about themselves, and — critically — what they can't do that Evenstar can. The output feeds our positioning, not just a spreadsheet.

Known competitors — starting intel

Pre-populated from initial recon. Priority tier reflects overlap risk with Evenstar's target client profile (boutique professional services, family-owned businesses, nonprofits, ~10–75 endpoints).

Four Winds IT
📍 Sarasota (+ Tampa, Ft. Myers, Orlando)
HIGH PRIORITY 200+ clients Since 2014
Most direct overlap. Explicitly targets legal, accounting, nonprofits, real estate in Sarasota. Claims 15-min avg response, 4.9★ Google, 180+ local businesses. Published tiered cybersecurity pricing ($30–120/user/mo). No long-term contracts is their pitch. Founded by Don Borden. Active on social. Watch closely.
Alliance IT
📍 Sarasota (722 Apex Rd)
HIGH PRIORITY 18 yrs (est. 2007) Rebranded from Suncoast
Well-established, chamber-active. Manatee Chamber member. Targets healthcare, construction, manufacturing, financial services. Touts vCISO-type positioning. Valspar Championship tech partner (2024). Decent brand presence. Legacy clients likely locked in long-term.
PCS Florida
📍 Sarasota, Vero Beach, Jacksonville
MED PRIORITY Since 2000 Multi-location
Regional growth mode. Recently expanded to Jacksonville, acquired ACT Computers (Vero Beach). 30-second live helpdesk answer is their differentiator. Manufacturing vertical focus. Their scale (3+ offices) may mean they're losing the boutique feel — angle there.
SCYBER
📍 Venice, FL
MED PRIORITY Since 2006 2–10 employees
Boutique, Venice-centric. Finance, insurance, construction, property mgmt focus. Explicitly pitches "small team that knows your environment" — directly competitive with our positioning. Venice Chamber + North Port Chamber member. Worth attending their chambers. Small enough to lose clients to us.
SWFIT
📍 Lakewood Ranch (+ Boston, MA)
MED PRIORITY LWRBA member Per-user flat rate
Newer, aggressive in LWR. Southwest Florida IT, CEO Nicholas Salem. Healthcare, financial services, professional services focus. Security-first messaging. LWRBA member — Ryan Patton should check if they're at those events. Co-managed + fully managed both offered.
Next Level IT Pros
📍 Lakewood Ranch
MED PRIORITY 25+ yrs exp claimed LWRBA member
SMB-focused, flat-rate. M365 + Teams VOIP specialist. Satisfaction guarantee language heavy. LWRBA member, active blog. Relatively thin web presence vs. Four Winds. May be punching above their weight on marketing vs. delivery.
Current Technologies
📍 Sarasota (HQ: Lombard, IL)
LOW PRIORITY 11–50 employees IL-based expansion
Out-of-state company with local office. Physical security / gunshot detection differentiator is unusual. Chicago HQ with Sarasota satellite — may lack deep local roots. Sarasota Chamber member. Schools and government in their vertical mix. Less threat to our core market.
Digital Defence LLC
📍 Venice, FL
LOW / UNKNOWN Thin web presence
Needs direct recon. Virtually no web footprint found. Could be a one-person shop or very new. May be operating entirely through referrals/word of mouth. Worth asking about at Venice Chamber events. Look up ownership on Sunbiz.org. Don't underestimate — lean operations can undercut on price.
Note on priority tiers: HIGH = direct overlap with Evenstar's ICP and active in the same chambers/territory. MED = partial overlap or adjacent territory. LOW = limited intel or minimal threat to our core accounts now. Tiers should be revised as Ryan fills out capture forms.

What to look for

These are the intelligence categories that actually move the needle for positioning, whitespace identification, and chamber networking. Each has specific things to watch for online vs. in person.

01
Messaging & Positioning
  • What's their main value prop headline?
  • Do they lead with price, speed, security, or relationship?
  • What words do they avoid? (e.g., compliance, vCISO, nonprofit)
  • Is their tone corporate or approachable?
  • Do they claim certifications prominently? (CISM, CEH, etc.)
02
Target Verticals
  • What industries do they list on their website?
  • Do they have dedicated landing pages for verticals?
  • What's conspicuously absent? (nonprofits, family businesses, professional services)
  • Are their testimonials from businesses that look like your clients?
  • What size client do they seem built for?
03
Pricing Signals
  • Do they publish any pricing? Per-seat, per-device, or tiered?
  • Four Winds reference: $30–50 / $50–80 / $80–120 per user/mo for security tiers
  • Do they lead with "flat rate" or "custom quote"?
  • Any mention of contract length? (3-year lock-in = weakness)
  • At events: listen for complaints about previous provider's pricing surprises
04
Service Stack Signals
  • Do they mention specific tools? (RMM, PSA, backup vendors)
  • Do they offer VoIP / phone systems?
  • Any mention of co-managed IT? (signals they target companies with internal IT)
  • Compliance/CMMC/HIPAA — do they go there?
  • Custom software dev? (Four Winds does — unusual)
05
Sales Motion & Lead Gen
  • Do they offer a free assessment, audit, or "30-min consult"?
  • What CTAs do they use? (Call us / Book online / Free guide download)
  • Are they running Google Ads? (search their name + check ads)
  • Do they have gated content (lead magnets)?
  • How fast do they follow up? (Have Ryan do a ghost inquiry on 1–2 competitors)
06
Reputation & Reviews
  • Google review count and star rating
  • What do negative reviews say? (response time, communication, billing)
  • Are reviews from real-looking local businesses?
  • LinkedIn follower count + post frequency
  • Chamber tenure — long-time members have relationship moats
07
Team Size & Capacity
  • LinkedIn employee count (rough signal)
  • Do they have named techs vs. anonymous helpdesk?
  • Are they hiring? (Indeed/LinkedIn jobs = growth signal)
  • Solo operators are different threat — flexible pricing, personal relationships
  • Any subcontracting or white-label signs?
08
Chamber / Community Presence
  • Which chambers are they members of?
  • Are they sponsors or just members?
  • Do they show up at events, or just list themselves?
  • Any board positions or leadership roles? (= relationship moat)
  • At events: how do they introduce themselves? What's their one-liner?
09
Whitespace Indicators
  • Are there verticals no one is loudly claiming? (arts orgs, law firms under 10 users, nonprofits)
  • Any geographic gaps in Manatee / Charlotte coverage?
  • Is compliance (HIPAA, CMMC-adjacent) being left on the table?
  • Which competitors seem to have no nonprofit clients?
  • Who's ignoring the family-owned business segment?

Chamber & alliance targets

These are the primary organizations worth joining or attending in the tricounty area. Joining before recon is complete is fine — dual-purpose presence. The goal is visibility + intel, not just one.

Greater Sarasota Chamber
Largest chamber. Alliance IT and Current Technologies are members. High-value for professional services. Ambassador program worth looking into.
Lakewood Ranch Business Alliance (LWRBA)
SWFIT and Next Level IT Pros are both members here. Fast-growing corridor. Heavily tech-savvy, growth-stage businesses. High density of target clients.
Venice Area Chamber
SCYBER is a member here. Venice Chamber is tight-knit and referral-heavy. Good for face-time recon on SCYBER. Smaller, more accessible community.
North Port Area Chamber
SCYBER also listed here. Charlotte County adjacent. Growing fast. Few MSPs with a loud presence yet — possible early-mover opportunity.
Manatee Chamber of Commerce
Alliance IT (LLC) has Bradenton roots and is a member. Bradenton + Palmetto businesses. Evenstar is Bradenton-based — home turf credibility here.
Englewood / Charlotte County EDC
Lower competitor density observed. Charlotte County is tricounty but underserved by MSPs in the research so far. Worth scoping as a longer-term expansion foothold.
Prioritization suggestion: Start with LWRBA (highest density of target prospects + known competitors) and Manatee Chamber (home turf). Venice and North Port are lower effort, higher intel value specifically for SCYBER recon. Don't over-commit memberships before you know which groups actually generate conversations.

Competitor intelligence log

Fill out one form per competitor, per research session. Hit Export Filled PDF to generate a clean named file with only the fields you've answered — blank fields are omitted.

Competitor Entry

One form per competitor · Export generates a named PDF with only answered fields

Basic Information
Messaging & Positioning
Pricing Signals
Services & Stack
Reputation & Online Presence
Competitive Scoring (1 = weak, 5 = strong)
Qualitative Notes
Exports only answered fields — skips blanks.

Evenstar MSP · Internal Use Only · Tricounty Competitor Intelligence v1.1
Completed PDFs should be stored in Hudu under the Evenstar internal documentation space. Aggregate findings reviewed quarterly.