Bridgehead Prepared for James at Fernstone
For James

Business Insurance Sales Playbook

James, we’ll build your new SDR’s first 100 accounts in 10 days. The first 25 are below, and they’re yours either way.

If your Founding Sales Development Representative seat stays open another quarter, ignore this. If it doesn’t, the next two minutes are worth it.

What we noticed

Your Founding SDR posting says you went from 0 to 500+ customers this year, with an average sales cycle of 15 days.

Your Founding SDR role was posted on September 24 and is still open on November 9; the posting asks the hire to create and own the outbound channel and book meetings by phone.

  1. January 8 Pre-seed round reported by Signalbase
  2. February 9 Launch post on Fondo: first customers
  3. September 24 Founding SDR posting first published
  4. November 9 Role still open; the first 25 accounts are on this page

What changes for your new AE

Your new SDR starts day one with 100 accounts you approved and drafts written to the first five, instead of spending their first weeks finding who to call. Your posting asks them to own outbound and turn calls into booked meetings; this gives them the list to start dialing and the reason to open each call. With deals closing in about 15 days, every week saved on finding accounts is a week sooner to their first booked meeting.

Your first 25 accounts

Picked from how your site and your posting describe your buyers. Each one has the reason it’s here and the source.

Yours either wayKeep these 25 whether or not we ever talk.
Cut any you wouldn’t callTell us why, and we replace it. We keep going until you’d keep at least 80 of the 100.
  1. TREW Capital Management New York, NY · 5 restaurants taken over
    1

    Five restaurants change hands at once, so five sets of liquor, payroll and landlord requirements need coverage under a new owner, and your bars page promises speed at an opening.

    Signal: Oct 22, 2026 Source
    Buyer: Principal at TREW Capital
    Why it’s ranked here

    A strong fit.

    • In a business Fernstone has a page for: security guards, fire and life safety, roofers and trades, pest control, garage, staffing, bars, nightlife or hotels.
    • Owner-led, with crews, shifts or hourly staff, so workers' comp, general liability and vehicles are the exposure.
    • A contract, lender, landlord or license that demands proof of coverage: certificates, additional insured status, limits.
    • Something changed in the last nine months: a new location, an acquisition, a contract award, a reopening or a sale.
    • Independent or a small platform, not a national company that places its own insurance program.
    • Looks like the 500+ businesses already served: the trades, security and hospitality, ideally in the New York area.
  2. Vision Security Corporation Brooklyn, NY · size not stated
    2

    A city guard contract is the kind your security page says creates insurance requirements that are easy to miss, and this one was awarded this summer.

    Signal: Aug 24, 2026 Source
    Buyer: Owner or president
    Why it’s ranked here

    A strong fit.

    • In a business Fernstone has a page for: security guards, fire and life safety, roofers and trades, pest control, garage, staffing, bars, nightlife or hotels.
    • Owner-led, with crews, shifts or hourly staff, so workers' comp, general liability and vehicles are the exposure.
    • A contract, lender, landlord or license that demands proof of coverage: certificates, additional insured status, limits.
    • Something changed in the last nine months: a new location, an acquisition, a contract award, a reopening or a sale.
    • Independent or a small platform, not a national company that places its own insurance program.
    • Looks like the 500+ businesses already served: the trades, security and hospitality, ideally in the New York area.
  3. Bar Cosme New York, NY (NoHo) · 1 bar
    3

    A new bar in a leased Lafayette Street space is the liquor, tipped-payroll and landlord-requirement mix your bars page describes, and it opens now.

    Signal: Nov 9, 2026 Source
    Buyer: Owner group behind Cosme
    Why it’s ranked here

    A strong fit.

    • In a business Fernstone has a page for: security guards, fire and life safety, roofers and trades, pest control, garage, staffing, bars, nightlife or hotels.
    • Owner-led, with crews, shifts or hourly staff, so workers' comp, general liability and vehicles are the exposure.
    • A contract, lender, landlord or license that demands proof of coverage: certificates, additional insured status, limits.
    • Something changed in the last nine months: a new location, an acquisition, a contract award, a reopening or a sale.
    • Independent or a small platform, not a national company that places its own insurance program.
    • Looks like the 500+ businesses already served: the trades, security and hospitality, ideally in the New York area.
  4. Beyond Pest Control Astoria and Manhattan, NY · 2 offices
    4

    A new office and overnight calls put techs in restaurants and buildings after hours, which is when property managers and landlords ask for certificates.

    Signal: Nov 6, 2026 Source
    Buyer: Owner
    Why it’s ranked here

    A strong fit.

    • In a business Fernstone has a page for: security guards, fire and life safety, roofers and trades, pest control, garage, staffing, bars, nightlife or hotels.
    • Owner-led, with crews, shifts or hourly staff, so workers' comp, general liability and vehicles are the exposure.
    • A contract, lender, landlord or license that demands proof of coverage: certificates, additional insured status, limits.
    • Something changed in the last nine months: a new location, an acquisition, a contract award, a reopening or a sale.
    • Independent or a small platform, not a national company that places its own insurance program.
    • Looks like the 500+ businesses already served: the trades, security and hospitality, ideally in the New York area.
  5. Brooklyn Pacha Brooklyn, NY · 1 venue
    5

    A 2,600-person room with bar service and a large night staff is the crowd, alcohol and occupancy exposure your nightlife page lists, and the doors opened this week.

    Signal: Nov 2, 2026 Source
    Buyer: Venue operator
    Why it’s ranked here

    A strong fit.

    • In a business Fernstone has a page for: security guards, fire and life safety, roofers and trades, pest control, garage, staffing, bars, nightlife or hotels.
    • Owner-led, with crews, shifts or hourly staff, so workers' comp, general liability and vehicles are the exposure.
    • A contract, lender, landlord or license that demands proof of coverage: certificates, additional insured status, limits.
    • Something changed in the last nine months: a new location, an acquisition, a contract award, a reopening or a sale.
    • Independent or a small platform, not a national company that places its own insurance program.
    • Looks like the 500+ businesses already served: the trades, security and hospitality, ideally in the New York area.
  6. CET Energy Solutions Massachusetts, with operations in 10 states · 400+ employees
    6

    Electrical crews tied to general contractors and tenant fit-outs are what your contractors page covers, and the acquired firms' policies now have to line up under one platform.

    Signal: Oct 28, 2026 Source
    Buyer: CEO
    Why it’s ranked here

    A strong fit.

    • In a business Fernstone has a page for: security guards, fire and life safety, roofers and trades, pest control, garage, staffing, bars, nightlife or hotels.
    • Owner-led, with crews, shifts or hourly staff, so workers' comp, general liability and vehicles are the exposure.
    • A contract, lender, landlord or license that demands proof of coverage: certificates, additional insured status, limits.
    • Something changed in the last nine months: a new location, an acquisition, a contract award, a reopening or a sale.
    • Independent or a small platform, not a national company that places its own insurance program.
    • Looks like the 500+ businesses already served: the trades, security and hospitality, ideally in the New York area.
  7. Select Exterminating Franklin Square, NY · 3 businesses acquired
    7

    Three acquired companies in two states bring three sets of vehicles, techs and commercial accounts that need one program, and your pest control page covers this trade.

    Signal: Aug 3, 2026 Source
    Buyer: Owner or CEO
    Why it’s ranked here

    A strong fit.

    • In a business Fernstone has a page for: security guards, fire and life safety, roofers and trades, pest control, garage, staffing, bars, nightlife or hotels.
    • Owner-led, with crews, shifts or hourly staff, so workers' comp, general liability and vehicles are the exposure.
    • A contract, lender, landlord or license that demands proof of coverage: certificates, additional insured status, limits.
    • Something changed in the last nine months: a new location, an acquisition, a contract award, a reopening or a sale.
    • Independent or a small platform, not a national company that places its own insurance program.
    • Looks like the 500+ businesses already served: the trades, security and hospitality, ideally in the New York area.
  8. Superior Roofing Alfred and Casco, ME · 2 new locations
    8

    Two new yards mean new crews and a growing payroll on roofs, the height and workers' comp exposure your roofers page says many carriers avoid.

    Signal: Oct 13, 2026 Source
    Buyer: Owner
    Why it’s ranked here

    A strong fit.

    • In a business Fernstone has a page for: security guards, fire and life safety, roofers and trades, pest control, garage, staffing, bars, nightlife or hotels.
    • Owner-led, with crews, shifts or hourly staff, so workers' comp, general liability and vehicles are the exposure.
    • A contract, lender, landlord or license that demands proof of coverage: certificates, additional insured status, limits.
    • Something changed in the last nine months: a new location, an acquisition, a contract award, a reopening or a sale.
    • Independent or a small platform, not a national company that places its own insurance program.
    • Looks like the 500+ businesses already served: the trades, security and hospitality, ideally in the New York area.

Your new SDR’s first 100 accounts, in 10 days

The first 25 are above, and they’re yours either way.

Email Kash

We build a handful of these a month, for founders hiring now.

10 days

from kickoff to your team running it

  • 100 accounts you approve, each with the reason
  • Drafts to the first five, in your voice
  • Your team runs it without us
  • Any account you cut, we replace

How does Fernstone sell?

An outside read from your site, your Founding SDR posting, your Y Combinator profile and your launch coverage, built to be corrected: tell us anything that’s wrong. Tap a clip to play it from that moment.

In your posts and interviews23 quotes
  1. Who buys
    “Today, we manage risk for 500+ businesses in construction, security, and the trades.”
    Y Combinator company page
  2. Who buys
    “Security businesses often lose time and money because insurance requirements are confusing, unrealistic, or easy to miss.”
    fernstone.com/security
  3. Who buys
    “we are just as comfortable helping a smaller local firm as we are supporting a larger, more complex operation.”
    fernstone.com/industrial-staffing
  4. Who buys
    “From full-service dining and neighborhood bars to breweries, lounges, catering, and multi-location groups”
    fernstone.com/bars-and-restaurants
  5. Who buys
    “You value a straightforward relationship with your insurance broker.”
    fernstone.com/working-with-fernstone
  6. Who buys
    “You want a quote without sharing meaningful details about your business.”
    fernstone.com/working-with-fernstone
  7. The problem
    “their insurance brokers rarely picked up the phone when they needed coverage for injured workers.”
    Fondo: Fernstone Launches, February 9
  8. The problem
    “Insurance brokers call, email, and even fax carriers for quotes. That back and forth is both manual and slow.”
    Fondo: Fernstone Launches, February 9
  9. The problem
    “Insurance is a $1T category that still runs on pen and paper.”
    Founding Sales Development Representative posting, September 24
  10. The problem
    “You may need insurance to start a new client contract, satisfy a worksite requirement, or keep a deal moving without delay.”
    fernstone.com/industrial-staffing
  11. The problem
    “A lender may request evidence of coverage, a wedding planner may need a certificate, a liquor authority may ask for documentation, or a vendor may need to be added before work begins.”
    fernstone.com/hotels
  12. Why you win
    “Fernstone is built for speed, and most clients can expect quote turnaround in under 48 hours.”
    fernstone.com/hotels
  13. Why you win
    “an average sales cycle of 15 days”
    Founding Sales Development Representative posting, September 24
  14. Why you win
    “They combine AI with licensed brokers-in-the-loop to review and bind coverage.”
    Fondo: Fernstone Launches, February 9
  15. Why you win
    “Their AI agent automates the manual back and forth, tracking email threads, and instantly following up.”
    Fondo: Fernstone Launches, February 9
  16. Why you win
    “Every client gets a dedicated risk advisor who learns your operations and grows with you.”
    fernstone.com
  17. Why you win
    “A single platform to issue COIs, track claims, manage policies, and stay compliant without the back-and-forth.”
    fernstone.com
  18. Why you win
    “Fernstone can review contract insurance language, flag problem areas, explain what is required, and help drive compliance”
    fernstone.com/security
  19. When a store moves
    “That matters when you are closing on a property, refinancing, opening after a renovation, changing management, or trying to bind coverage before a peak-season deadline.”
    fernstone.com/hotels
  20. When a store moves
    “whether you are hiring, expanding into new states, taking on bigger contracts, or adding armed work over time.”
    fernstone.com/security
  21. When a store moves
    “Built to move at the speed of your opening.”
    fernstone.com/bars-and-restaurants
  22. When a store moves
    “I am friends with my current or former broker. Will they know I am shopping?”
    fernstone.com/loss-run-faq
  23. When a store moves
    “Not if you request your loss runs directly from the insurance carrier.”
    fernstone.com/loss-run-faq
What your customers sayFrom Fondo: Fernstone Launches
  1. ACas told in Fondo's launch post
    “One customer told them he waited 6 weeks for his broker to find him construction insurance. In that time, he lost a major deal.”
    A customer, as told in Fondo's launch post · Fondo: Fernstone Launches

Words you use

  • “Insurance for businesses that move fast”
  • “Risk management that grows with you”
  • “White-glove support”
  • “dedicated risk advisor”
  • “Transparent, competitive pricing”
  • “loss runs”
  • “Nuance prevents delays and gaps”
  • “Built to move at the speed of your opening”
  • “Built to protect every crew, ladder, trailer, and roof deck”
  • “Contract review before requirements become problems”
  • “brokers-in-the-loop”
  • “Active risk coverage”

How the list learns your calls

In the first session you react to accounts like these: keep or cut, and why, the way you’d tell a cofounder. Each reason becomes a rule you can read, the pool re-scores, and ten more show whether it learned. Keep eight of ten and the hundred is built on your rules.

  1. You cut one on the call, and say why
  2. It becomes a rule
  3. The pool re-scores
  4. Ten more test it

Which questions can only you answer?

Your site and your posting don’t say which businesses you’d never spend a call on, or what an owner has to see before they hand over their loss runs. About 30 minutes of you reacting to real accounts answers these.

  1. 1

    Does a new owner after an acquisition buy fast, or wait for the next renewal?

    Rows 6, 7 and 10 are all acquisitions; row 1 took over five restaurants at once.

  2. 2

    Is a hospitality opening a call for your SDR, or only for the trades?

    Rows 5 and 3 open this month; row 14 is a hotel with a new owner.

  3. 3

    Does a business that is part of a larger platform ever buy through you?

    Row 22 (JP McHale, owned by Anticimex) and row 23 (Landry's) stay or go on this one.

  4. 4

    Is a software vendor to guard companies a buyer or a way to reach many guard firms?

    Row 25 (Guardhouse) depends on it.

  5. 5

    Does the SDR work the New York region first, or the whole country?

    Rows 2, 1 and 9 are New York; row 8 is in Maine and row 12 is in Texas.

What does your Founding Sales Development Representative’s first morning look like?

Without

The CRM you have now. The early weeks go to learning which accounts you’d call, and why.

With · Founding Sales Development Representative, first morning

  • TCTREW Capital ManagementDraft written
  • VSVision Security CorporationDraft written
  • BCBar CosmeDraft written
  • BPBeyond Pest ControlDraft written
  • BPBrooklyn PachaDraft written

A hundred accounts you approved, the rules behind them and drafts to the first five, so their time goes to buyers.

From week two, your mornings too: one brief, drafts to approve, every message sent by you.

How the 10 days run

What happens in the ten working days?

November 16, 2026 to December 1, 2026. About a day of your time in total.

  1. Before by November 16

    You send the customers you’d clone and three deals that went wrong, plus 10 to 20 emails or posts you wrote. “How you sell” is drafted from your talks and posts.

    You: 20 minutes
  2. Day 1 November 16

    The playbook session: we fill the gaps and correct the draft together. Your CRM is connected.

    You: 2 hours
  3. Day 2 November 17

    Your first rules are written; a few hundred companies are scored against them.

    You: none
  4. Day 3 November 18

    You review the first 25 (talking it through is fine).

    You: 30 minutes
  5. Day 4 November 19

    Your reasons become rules; you see the re-score and judge 10 more. First touches are written in your voice to the accounts you kept, and you read ten. Touches start logging to the CRM.

    You: 30 minutes
  6. Day 5 November 20

    The hundred is built. The research tool is set up; you test it on three accounts you know.

    You: 15 minutes
  7. Day 6 November 23

    The morning run is set up; your first morning, with us.

    You: 30 minutes
  8. Day 7 November 24

    You review all hundred, and any cut is replaced. Team training, session one.

    You: 1 hour 20 minutes
  9. Day 8 November 25

    Your first morning on your own. Training session two, hands-on for each person.

    You: 1 hour plus your morning
  10. Day 9 November 30

    Your second morning on your own. Each person on your team runs the morning alone.

    You: your morning
  11. Day 10 December 1

    Your third morning on your own. A week of touches is in the CRM. Handover sign-off.

    You: 30 minutes plus your morning
Kash Badami

Who builds it?

The person in the video does the work with you, from the first session to the handover.

$100M+in deals sold in a single year
$0 to $10MARR in 12 months, for a company I built
  1. “Kash and I built ERT Credit together in 2021. He took my MVP and turned it into a SaaS that hit $10M ARR in twelve months.”

    Jordan Anderson, CEO, PayStreetgobridgehead.ai/about

  2. “Analytical in approach, technologically-knowledgeable, and earnest in conviction, Kash was able to drive pipeline in a notoriously challenging tech region.”

    JBJason Brandt, Managing Director, Sales, ePlus inc.LinkedIn recommendation, April 2020

Where does this go from here?

Three options. Each one is fine.

Not a fit

Say so in a line, and that’s the end of it.

Not now

Keep the 25 and the read on how you sell, and share them. When the role fills, the offer stands.

Talk with Kash

Ask Kash to call you, or email him. He calls to set up a 30-minute strategy session. Bring your cofounder or your sales leader.

Your new SDR’s first 100 accounts, in 10 days

The first 25 are above, and they’re yours either way.

Email Kash

We build a handful of these a month, for founders hiring now.

10 days

from kickoff to your team running it

  • 100 accounts you approve, each with the reason
  • Drafts to the first five, in your voice
  • Your team runs it without us
  • Any account you cut, we replace

Fernstone sales playbook, in brief

Fernstone is an AI-native insurance brokerage in New York that pairs AI with licensed brokers; its Y Combinator profile says it manages risk for 500+ businesses in construction, security and the trades.Y Combinator company page, Founding Sales Development Representative posting

Its pages sell speed and a dedicated advisor to owner-run businesses: a typical quote in under 48 hours, certificates and claims on one platform, and review of the contract insurance language that holds up a job.fernstone.com/security, fernstone.com/hotels, fernstone.com

The Founding Sales Development Representative posting asks the hire to create and own the outbound channel, reach prospects by phone, book meetings and stand up new verticals, with an average sales cycle of 15 days.Founding Sales Development Representative posting

The first 25 accounts for a new SDR are security, fire, pest, roofing, hospitality and staffing businesses, each scored on six rules and backed by a dated, sourced signal such as an acquisition, a city contract or a new opening: fourteen strong fits, seven in the middle and four edge cases that test the rules.

Prepared by at Bridgehead · November 9, 2026 · Every source

Questions founders ask

Can’t my SDR build this when they start?

They can. But wouldn’t you rather they were booking meetings? Reps spend 28% of their time selling, and the average SDR takes 3.0 months to ramp and stays 1.9 years. This replaces the weeks they would spend building the list and learning what you already know.

28%: Salesforce, State of Sales (7,700+ sellers, 2022) · 3.0 months: Bridge Group, 2025 SDR report (351 companies)

How much sooner does my new SDR get to work?

From day one, because the accounts you approved and the first drafts are waiting. The average SDR takes 3.0 months to ramp, and only 60% hit quota.

3.0 months: Bridge Group, 2025 SDR report (351 companies) · 60%: Bridge Group, 2025 SDR report (351 companies)

We tried an outreach tool and it sounded like a robot. How is this different?

Nothing goes out on its own. Every account on the list is one you approved, every draft is written to one person, and you send each message yourself. It learns your voice from what you’ve written and from every edit you make.

How much of my time does it take?

About a day, spread across the ten working days: the 2-hour session on how you sell, short list reviews you can talk through, two training sessions and your first mornings. The hours your SDR gets back go to selling, where reps spend just 28% of their time today.

28%: Salesforce, State of Sales (7,700+ sellers, 2022)

What happens after you leave?

It keeps learning. Each week it proposes rule changes from what your cuts, replies and silences showed, and you approve or reject each in a line.

Where does my data live?

In your own accounts: your Claude, your CRM, your files. Nothing runs on anyone else’s side, and any rule can be changed in plain English.

How is it priced?

The first engagement is one fixed price for the ten days. It depends on how many people we train and which systems we connect, so Kash quotes it on a short call. After handover, you can keep us on a retainer to keep supporting your sales process and refining it, if you choose that route.

The research behind this page 13 sources · 4 postings · 0 customers · 33 stores looked at

Your talks and posts

  1. fernstone.com
  2. fernstone.com/working-with-fernstone
  3. fernstone.com/loss-run-faq
  4. fernstone.com/security
  5. fernstone.com/hotels
  6. fernstone.com/bars-and-restaurants
  7. fernstone.com/contractors
  8. fernstone.com/roofers
  9. fernstone.com/industrial-staffing
  10. fernstone.com/nightlife
  11. Y Combinator company page
  12. Fondo: Fernstone Launches, February 9, 2026
  13. Signalbase: Fernstone funding, January 8, 2026

Your open roles

  1. Founding Sales Development Representative, first posted September 24, 2026
  2. Founding Growth & Operations Lead, first posted September 24, 2026
  3. Founding Growth & Operations Analyst, first posted September 27, 2026
  4. Founding Engineer, first posted September 27, 2026

Your customers

(santehq.com/customers and your posts). Customer photos are from santehq.com/customers.

How the 25 were picked

33 stores found and scored on 6 rules; the 25 chosen to teach: 14 strong, 7 middle, 4 at the edges. Logos are from each store’s own site.

  • Sources: your own site and verticals pages, your Founding SDR posting, your Y Combinator profile, Fondo's launch post, and trade press, city notices and local news for the 25 accounts, each opened and saved on November 9, 2026.
  • Your site names no customers, so none of the 25 could be matched against a customer list; none of the saved pages for the 25 mentions Fernstone.
  • We did not find a podcast, talk or LinkedIn post from you, so how you sell is read from your site, your posting and your launch coverage.
  • Eight first-draft accounts were dropped because their release pages would not open or had no usable date.
  • Where a source gives no store, room or employee count, the row says so.