Bridgehead Prepared for Rene at Casco
For Rene

Penetration Testing Sales Playbook

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

What we noticed

You announced a $100M valuation Series A on July 13, and your post says Casco found critical vulnerabilities in 400+ companies that already had code security tools and human pentesters.

Your SDR role has been posted since September 6, and the posting says the new hire will help build the outbound playbook.

  1. July 13 $100M valuation Series A announced, $17M raised in total
  2. August 31 Listed on the FedRAMP Marketplace
  3. September 6 SDR role posted
  4. November 9 SDR 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 the ramp building lists. Your posting gives them three months to ramp and says month one is for building account lists; this puts the list in their hands on the first morning, each with the reason to call now.

Your first 25 accounts

Picked from how you describe your buyers in your Series A post and your posting. 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. Decagon San Francisco · Series-stage; 130 open roles
    1

    Their posting names Avis Budget Group, Cash App and Chime as brands running its AI agents, and a security hire is being added now. That's the AI-agent scope you sell, and a security hire is the AppSec leader your posting says your SDR should open with.

    Signal: Sep 21, 2026 Source
    Buyer: Head of Security or the AppSec lead the posting reports into
    Why it’s ranked here

    A strong fit.

    • Ships software continuously, so a once-a-year test is already out of date by the time the report lands.
    • Builds AI agents, developer tools or SDKs: the AI apps and agents and tenant-isolation scopes you test.
    • Sells to enterprise or regulated customers whose security reviews gate deals.
    • Something changed in the last 90 days: a security hire posted, a funding round, a launch or a new compliance step.
    • Not a current Casco customer and not a security testing vendor.
    • Small enough that one security hire is a real decision: a startup or growth-stage security team, not a large security organization.
  2. Harvey San Francisco · 376 open roles
    2

    Harvey sells agentic AI to legal and professional services firms and is adding a second product security seat in three months. It's an enterprise-deal account of the kind SixtyFour describes in your customer quote.

    Signal: Oct 28, 2026 Source
    Buyer: Head of Security or product security lead
    Why it’s ranked here

    A strong fit.

    • Ships software continuously, so a once-a-year test is already out of date by the time the report lands.
    • Builds AI agents, developer tools or SDKs: the AI apps and agents and tenant-isolation scopes you test.
    • Sells to enterprise or regulated customers whose security reviews gate deals.
    • Something changed in the last 90 days: a security hire posted, a funding round, a launch or a new compliance step.
    • Not a current Casco customer and not a security testing vendor.
    • Small enough that one security hire is a real decision: a startup or growth-stage security team, not a large security organization.
  3. Replit Foster City, CA · 31 open roles
    3

    An agent that writes and runs code for millions of users is the exact surface your AI apps and agents testing covers. They're hiring an architect to own it, so the testing budget conversation is open now.

    Signal: Sep 1, 2026 Source
    Buyer: Head of Security or the new AI Agent Security Architect
    Why it’s ranked here

    A strong fit.

    • Ships software continuously, so a once-a-year test is already out of date by the time the report lands.
    • Builds AI agents, developer tools or SDKs: the AI apps and agents and tenant-isolation scopes you test.
    • Sells to enterprise or regulated customers whose security reviews gate deals.
    • Something changed in the last 90 days: a security hire posted, a funding round, a launch or a new compliance step.
    • Not a current Casco customer and not a security testing vendor.
    • Small enough that one security hire is a real decision: a startup or growth-stage security team, not a large security organization.
  4. WorkOS United States & Canada · 28 open roles
    4

    Authentication and identity APIs sit under other companies' enterprise logins. Two security hires on the same day says the program is being built now, and it's a developer-platform buyer like the one your SDK testing is for.

    Signal: Sep 23, 2026 Source
    Buyer: Head of Security or the product security lead
    Why it’s ranked here

    A strong fit.

    • Ships software continuously, so a once-a-year test is already out of date by the time the report lands.
    • Builds AI agents, developer tools or SDKs: the AI apps and agents and tenant-isolation scopes you test.
    • Sells to enterprise or regulated customers whose security reviews gate deals.
    • Something changed in the last 90 days: a security hire posted, a funding round, a launch or a new compliance step.
    • Not a current Casco customer and not a security testing vendor.
    • Small enough that one security hire is a real decision: a startup or growth-stage security team, not a large security organization.
  5. Temporal United States (Remote) · 82 open roles
    5

    A durable-execution platform that runs customers' code across multiple clouds has a tenant-isolation question, which is the test your SDK and sandbox work does. The hire is staff level, so the person who'd buy is being picked now.

    Signal: Oct 29, 2026 Source
    Buyer: Staff Application Security Engineer once hired, or the head of security
    Why it’s ranked here

    A strong fit.

    • Ships software continuously, so a once-a-year test is already out of date by the time the report lands.
    • Builds AI agents, developer tools or SDKs: the AI apps and agents and tenant-isolation scopes you test.
    • Sells to enterprise or regulated customers whose security reviews gate deals.
    • Something changed in the last 90 days: a security hire posted, a funding round, a launch or a new compliance step.
    • Not a current Casco customer and not a security testing vendor.
    • Small enough that one security hire is a real decision: a startup or growth-stage security team, not a large security organization.
  6. Sentry San Francisco · 41 open roles
    6

    A small security team protecting a product that ships constantly and holds customers' error data. Your continuous pentesting pitch is built for teams that can't hire fast enough.

    Signal: Aug 26, 2026 Source
    Buyer: Head of Security
    Why it’s ranked here

    A strong fit.

    • Ships software continuously, so a once-a-year test is already out of date by the time the report lands.
    • Builds AI agents, developer tools or SDKs: the AI apps and agents and tenant-isolation scopes you test.
    • Sells to enterprise or regulated customers whose security reviews gate deals.
    • Something changed in the last 90 days: a security hire posted, a funding round, a launch or a new compliance step.
    • Not a current Casco customer and not a security testing vendor.
    • Small enough that one security hire is a real decision: a startup or growth-stage security team, not a large security organization.
  7. Writer New York City · 46 open roles
    7

    A platform of autonomous agents sold to enterprise marketing and revenue teams is an agent-security and procurement-review account at once. Four security postings in one day says the program is expanding this week.

    Signal: Nov 3, 2026 Source
    Buyer: Head of Security
    Why it’s ranked here

    A strong fit.

    • Ships software continuously, so a once-a-year test is already out of date by the time the report lands.
    • Builds AI agents, developer tools or SDKs: the AI apps and agents and tenant-isolation scopes you test.
    • Sells to enterprise or regulated customers whose security reviews gate deals.
    • Something changed in the last 90 days: a security hire posted, a funding round, a launch or a new compliance step.
    • Not a current Casco customer and not a security testing vendor.
    • Small enough that one security hire is a real decision: a startup or growth-stage security team, not a large security organization.
  8. Rogo New York City · 100 open roles
    8

    The posting names investment banks, private equity funds and investment firms as clients. Two security roles, product and cloud, line up with the two scopes your platform tests together.

    Signal: Nov 5, 2026 Source
    Buyer: Head of Security
    Why it’s ranked here

    A strong fit.

    • Ships software continuously, so a once-a-year test is already out of date by the time the report lands.
    • Builds AI agents, developer tools or SDKs: the AI apps and agents and tenant-isolation scopes you test.
    • Sells to enterprise or regulated customers whose security reviews gate deals.
    • Something changed in the last 90 days: a security hire posted, a funding round, a launch or a new compliance step.
    • Not a current Casco customer and not a security testing vendor.
    • Small enough that one security hire is a real decision: a startup or growth-stage security team, not a large security organization.

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 Casco sell?

An outside read from your Series A post, your blog, your BSides post, your site and your posting, built to be corrected: tell us anything that’s wrong. Tap a clip to play it from that moment.

In your posts and interviews9 quotes
  1. Who buys
    “Then government security teams started showing up at our conference booths.”
    Your post: Casco is the first standalone FedRAMP-listed agentic offensive security platform, August 31
  2. The problem
    “An annual check cannot keep up with continuous software development”
    Your Series A post: Announcing our $100M valuation Series A, July 13
  3. The problem
    “Their attack surface was changing faster than annual assessments could track.”
    Your post: Casco is the first standalone FedRAMP-listed agentic offensive security platform, August 31
  4. The problem
    “they're just noisy security slop.”
    Your Series A post: Announcing our $100M valuation Series A, July 13
  5. The problem
    “83 percent of security professionals feel completely burnt out by their workload.”
    Your Series A post: Announcing our $100M valuation Series A, July 13
  6. The problem
    “If you ask any security engineer at any company if they have full security coverage over their entire attack surface area, they will say no.”
    Your Series A post: Announcing our $100M valuation Series A, July 13
  7. Why you win
    “You cannot validate a software's security while being completely detached from its runtime reality.”
    Your Series A post: Announcing our $100M valuation Series A, July 13
  8. Why you win
    “Casco already found critical vulnerabilities in 400+ companies despite them using the popular code security tools and human pentesters.”
    Your Series A post: Announcing our $100M valuation Series A, July 13
  9. When a store moves
    “Their code and software were growing at an unprecedented rate.”
    Your post: Casco is the first standalone FedRAMP-listed agentic offensive security platform, August 31
What your customers sayFrom Sales Development Representative posting, casco.com
  1. CSCasco SDR posting
    “AppSec leaders and CISOs who know annual pentests and noisy security scanners cannot keep up with how quickly modern teams ship software”
    Casco SDR posting · Sales Development Representative posting
  2. SSCEO, SixtyFour
    “Casco is mission-critical for enterprise deals. We started the security assessment on a Friday and completed the procurement process by Monday.”
    Saarth Shah, CEO, SixtyFour · casco.com
  3. Ccasco.com
    “Casco pentest reports have cleared the toughest procurement processes at Microsoft, Google, AMD, and Apple.”
    casco.com · casco.com
  4. Ccasco.com
    “Every finding validated at runtime with authenticated test users, prioritized based on your application's context.”
    casco.com · casco.com
  5. BCCEO, Scout
    “In a matter of hours, Casco was able to find critical vulnerabilities that our other pentesters couldn't find for months.”
    Bryan Chappell, CEO, Scout · casco.com
  6. Ccasco.com
    “Share pentest reports, remediation status, and retest evidence to keep customer security reviews moving.”
    casco.com · casco.com
  7. CSCasco SDR posting
    “Work events: Attend security events with the team, start conversations in the room, and follow up fast enough to turn interest into pipeline.”
    Casco SDR posting · Sales Development Representative posting

Words you use

  • “continuous offense”
  • “noisy security slop”
  • “effortlessly secure”
  • “agentic security engineer”
  • “last line of defense”
  • “annual pentests”
  • “authenticated test users”
  • “false positives”

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 posts and your posting say what a good meeting looks like. They don’t say which companies you’d never spend one on, or what a security leader has to see before taking the call. About 30 minutes of you reacting to real accounts answers these.

  1. 1

    Does a company with an in-house red team ever buy?

    Row 22 (Cloudflare) has an AI red team posting open; your answer keeps or cuts it and anything like it.

  2. 2

    Do you sell to security leaders who own AI agent risk differently from AppSec?

    Rows 20 (Perplexity) and 3 (Replit) post agent-security and governance roles rather than plain AppSec.

  3. 3

    Is an unfilled security posting a reason to call now, or a reason to wait for the hire?

    Rows 11 (Render) and 15 (Cognition) posted manager-level security roles in the last week; row 7 (Writer) posted four.

  4. 4

    Does a partner like Anthropic count as an account?

    Row 25 (Anthropic) is on your Cyber Verification Program list.

What does your 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 · Sales Development Representative, first morning

  • DDecagonDraft written
  • HHarveyDraft written
  • RReplitDraft written
  • WWorkOSDraft written
  • TTemporalDraft 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

Casco sales playbook, in brief

Casco sells continuous AI pentesting and application security to software companies, with every finding validated against the running product. Rene Brandel announced a $100M valuation Series A on July 13 that brought total funding to $17M.Your Series A post: Announcing our $100M valuation Series A, casco.com

Its security buyers are AppSec leaders and CISOs who know annual pentests and noisy scanners can't keep up, and its customers describe finding critical vulnerabilities in hours and clearing procurement in days.Sales Development Representative posting, casco.com

The open SDR role asks for someone to start conversations with AppSec leaders, work security events and help build the outbound playbook; government teams also found Casco at conference booths.Sales Development Representative posting, Your post: Casco is the first standalone FedRAMP-listed agentic offensive security platform

The first 25 accounts for a new SDR are software and AI companies with a security role posted on their own job board, each scored on six rules with a dated source: fifteen strong fits, six 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 11 sources · 1 postings · 13 customers · 36 stores looked at

Your talks and posts

  1. Your Series A post: Announcing our $100M valuation Series A, July 13, 2026
  2. casco.com, November 9, 2026
  3. Your post: Casco is the first standalone FedRAMP-listed agentic offensive security platform, August 31, 2026
  4. Your post: We hacked Y Combinator's AI agents, May 27, 2025
  5. Your post: The 5 Levels of Penetration Testing, January 5, 2026
  6. CrewAI Uses Casco to Test the Security of AI Agents, May 28, 2025
  7. Your post: How We Hire, January 18, 2026
  8. Your LinkedIn post on the BSides talks, October 28, 2026
  9. Your post: Our Policy on Clean Pentest Reports, April 12, 2026
  10. AI Native Dev podcast: The Hidden Vulnerabilities Behind AI Code, with Simon Maple
  11. Your post: 5 Things to Compare Before Choosing a Pentest Quote, September 10, 2026

Your open roles

  1. Sales Development Representative, first posted September 6, 2026

Your customers

CrewAI · Scout · SixtyFour · Archil · Baseten · Daytona · Gusto · Levels.fyi · Microsoft · Novig · Spreedly · Substack · Whop (santehq.com/customers and your posts). Customer photos are from santehq.com/customers.

How the 25 were picked

36 stores found and scored on 6 rules; the 25 chosen to teach: 15 strong, 6 middle, 4 at the edges. Logos are from each store’s own site.

  • Sources: Casco’s own site and blog, its SDR posting (read through the Ashby posting API), the founder’s LinkedIn post, and each account’s own job posting, each opened and saved on November 9, 2026.
  • 36 software companies with a public security posting on their own job boards were looked at; the 25 chosen teach the rules.
  • None of the 25 appears among the 13 customer logos on casco.com, and none of their sites mentions Casco. Two companies that did (Baseten, Gusto) were dropped.
  • A posting is a dated sign that a security seat is being filled. It doesn’t say who owns the testing budget, so buyer titles are roles, not names.
  • Casco’s own pages give 400+ companies in the Series A post and 300+ in the posting; the page uses the Series A post.