Sidekick Security

What Sidekick Security does

Sidekick Security is an AI-native cybersecurity consulting firm headquartered in Bethesda, MD, founded in January 2026 by Robert Wood (former CISO at the Centers for Medicare and Medicaid Services, 2020–2024) and Taylor Pierce (former full-stack GTM leader at Praetorian with 15 years in offensive security). The firm delivers consulting across four service pillars—AI Security (covering AI red teaming, MITRE ATLAS threat modeling, agent security architecture, and AI supply chain risk), Program Transformation (the MAP assessment), Offensive Security (penetration testing, red teaming, cloud and mobile security validation), and Continuous Security (the vSec embedded partnership)—to SMB, mid-market, enterprise, healthcare, and government clients. Named customers include Anthropic, Asana, Box, Retool, CRIO, Anomali, and On Running, with additional case-study work for unnamed Fortune 500 financial services companies, a global retailer, multi-hospital health systems, healthcare SaaS companies, federal healthcare agencies, fintechs, and a 30,000-student public school district.

The firm's service delivery is supported by a proprietary AI-native platform of pre-built tooling that is deployed as part of every engagement. The platform includes automated compliance evidence collection mapped to SOC 2, HIPAA, FedRAMP, and ISO 27001 controls; pre-built SIEM detection rule packs for cloud misconfigurations, identity attacks, and lateral movement; continuous external attack surface discovery; AI-powered offensive security agents that simulate adversary behavior; AI-assisted alert triage and log analysis; and maturity scorecards benchmarked against NIST CSF and CIS Controls. Sidekick has also released a public-facing Trust Map interactive tool (trust-map.sidekicksecurity.io) and produces content via blog and a weekly podcast to support top-of-funnel thought leadership.

Revenue is generated through two primary streams: SOW-based professional services consulting engagements and the Continuous Security (vSec) subscription model pairing a senior security leader with a forward-deployed engineer across a phased Assess–Build–Optimize structure. Pricing is quote-based and not publicly disclosed. The firm operates without a traditional sales team, instead relying on the Sidekick Syndicate—an invite-only referral network of vCISOs, practitioners, consultants, and former executives who earn 10% uncapped commissions on closed deals—as its primary go-to-market motion. All engagements are founder-led, and the firm explicitly avoids building layered account-manager or junior-analyst structures in favor of investing in senior practitioner capacity.

Name

Sidekick Security

Legal name

Sidekick Security, LLC

Website

https://sidekicksecurity.io

Company type

Private

Founded year

2026

Operating status

Operating

Headcount range

11–50 employees

Short description

Sidekick Security is an AI-native cybersecurity consulting firm serving SMB, mid-market, enterprise, healthcare, and government clients. Founded by former CMS CISO Robert Wood and former Praetorian GTM leader Taylor Pierce, it delivers four service pillars (AI Security, Program Transformation, Offensive Security, Continuous Security) via proprietary tooling and embedded senior practitioners.

Ownership category

akta.pro rank

Product category

Cybersecurity Consulting

NAICS

Investigation and Security Services (5616), Computer Systems Design and Related Services (54151), Security Systems Services (56162)

SIC

Services-Computer Integrated Systems Design (7373), Services-Prepackaged Software (7372)

akta.pro primary industry

Penetration Testing & Red Teaming (BPAKADAE)

akta.pro secondary industries

Threat Intelligence, Hunting & Adversary Emulation (BPAKAHAE), Vulnerability Management & Penetration Testing Services (BPAEADAD), Cybersecurity Operations Outsourcing (SOC / SecOps) (BPAEAMAG)

Keywords

• Cybersecurity consulting
• AI security services
• Offensive security testing
• Security program transformation
• Compliance and GRC services

Headquarters

HQ city

Bethesda

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2B

Offering type

Services

Cost components

Personnel, Technology or R&D, Operations, Marketing or Sales, Others

Revenue model

1. Professional Services Consulting: Cybersecurity consulting engagements including AI Security, Program Transformation, and Offensive Security services. Delivered through structured engagements with deliverables and milestones as outlined in Statements of Work.
2. Continuous Security (vSec): Ongoing security partnership model pairing a senior security leader with a forward-deployed engineer. Provides continuous security leadership, tool deployment, and program optimization. Structured in phases: Assess & Plan (months 1-2), Build & Harden (months 2-12), Optimize & Scale (12+ months).

Go-to-market motion1 record

Distribution channels3 records

Marketing channels6 records

Core offering

Sidekick Security is an AI-native cybersecurity consulting firm that delivers four core service pillars — AI Security, Program Transformation (MAP), Offensive Security, and Continuous Security (vSec) — supported by a proprietary platform of pre-built tooling, automation, and integrations. Engagements combine senior practitioner expertise with AI-driven automation for compliance evidence collection, detection engineering, attack surface discovery, maturity assessments, and adversary simulation, with founders personally leading every client relationship.

Product overview

Sidekick Security is an AI-native cybersecurity consulting firm offering four core service pillars — AI Security, Program Transformation (MAP), Offensive Security, and Continuous Security (vSec) — supported by a proprietary Platform of pre-built solutions and automation. The firm's model combines human expertise with AI-native tooling, embedding senior practitioners alongside forward-deployed engineers who deploy the platform's pre-built capabilities (compliance evidence collection, detection rules, playbooks, cloud baselines, dashboards, scorecards) from day one. The Maturity Action Plan (MAP) serves as the entry-point assessment deliverable, while vSec provides an ongoing embedded partnership. This service-plus-tooling architecture contrasts with traditional consulting by delivering actionable outcomes rather than reports alone.

Differentiator

Problem solved

Functional benefit

Brands

• vSec (Continuous Security): Ongoing security partnership combining a senior security leader with a forward-deployed engineer, backed by pre-built tooling and automation.
• MAP (Maturity Action Plan)

Products and services

• AI Security Comprehensive AI risk management service including red teaming, threat modeling with MITRE ATLAS, agent security architecture, and AI supply chain security for organizations deploying AI systems.
• Program Transformation (MAP) Security program maturity assessment and strategic modernization service providing a complete maturity roadmap in 4-6 weeks.
• Offensive Security Penetration testing and adversary simulation across web apps, APIs, mobile, cloud infrastructure, and networks, including red team and purple team exercises.
• Continuous Security (vSec) Ongoing embedded security partnership combining a senior security leader with a forward-deployed engineer across three structured phases.

Quantifiable outcome

• One client achieved 40% tool reduction while improving detection coverage
• +20 more outcomes

Named customers24 records

Segments5 records

Ideal customer profiles5 records

Technology focussed Yes

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

AI capability8 records

Feature6 records

Partnerships

Ten partnerships are on record, tiered core and minor.

• AnthropiccoreTechnology or IntegrationStrategic partnership for HIPAA-ready AI security. Sidekick Security leverages Anthropic's AI technology to help health systems deploy AI safely with governance frameworks, risk assessments, and technical controls that scale across clinical and operational use cases.
• AnomaliminorOthersCustomer logo displayed on website indicating work relationship. Anomali appears in the 'Organizations We've Worked With' and 'Trusted by Companies' sections.
• AsanaminorOthersCustomer logo displayed on website indicating work relationship. Asana appears in the 'Organizations We've Worked With' and 'Trusted by Companies' sections.
• BoxminorOthersCustomer logo displayed on website indicating work relationship. Box appears in the 'Organizations We've Worked With' and 'Trusted by Companies' sections.
• CRIOminorOthersCustomer logo displayed on website indicating work relationship. CRIO appears in the 'Organizations We've Worked With' and 'Trusted by Companies' sections.
• On RunningminorOthersCustomer logo displayed on website indicating work relationship. On Running appears in the 'Organizations We've Worked With' and 'Trusted by Companies' sections.
• RetoolminorOthersCustomer logo displayed on website indicating work relationship. Retool appears in the 'Organizations We've Worked With' and 'Trusted by Companies' sections.
• WizminorOthersPartner logo displayed on About page indicating technology partnership or customer relationship. Wiz appears in the 'Organizations We Work With' section.
• SeezominorOthersPartner logo displayed on About page indicating technology partnership or customer relationship. Seezo appears in the 'Organizations We Work With' section.
• Boost SecurityminorOthersPartner logo displayed on About page indicating technology partnership or customer relationship. Boost Security appears in the 'Organizations We Work With' section.

Scale indicators1 record

Recent moves5 records

Expansion highlights6 records

Broad incumbents

• Secureworks: Secureworks is a global managed security and consulting provider covering offensive security, MDR, and GRC advisory. It competes with Sidekick's Continuous Security and Offensive Security pillars at the enterprise tier.
• NCC Group / NCC Cybersecurity: NCC Group is a global, publicly-traded cybersecurity firm offering offensive security, GRC advisory, and managed detection across the same customer segments. It competes with Sidekick at the enterprise end and provides a useful benchmark for what a scaled version of the model looks like.
• Optiv: Optiv is a large cybersecurity solutions integrator and advisory firm delivering GRC, offensive security, and managed services to mid-market and enterprise buyers. It is comparable as a broad incumbent competing for the same program-transformation wallet.
• Mandiant (Google Cloud): Mandiant is a global incident-response and cybersecurity advisory leader offering offensive security, threat intelligence, and program transformation. It competes with Sidekick at the enterprise and government tier with overlapping offensive-security and AI-risk narratives.

Direct peers

• A-LIGN: A-LIGN is a cybersecurity compliance and advisory firm focused on SOC 2, ISO 27001, HITRUST, PCI, and FedRAMP for SMB and mid-market clients. It directly overlaps Sidekick's compliance-led Program Transformation and SMB/mid-market customer base.
• Praetorian: Praetorian is a direct peer founded on offensive security services and now expanded into broader cybersecurity consulting, AI/ML risk, and managed security. Co-founder Taylor Pierce previously built Praetorian's GTM organization, making it the closest comparable in service mix, target market, and delivery model.
• Tevora: Tevora is a specialized security and privacy consultancy providing offensive security, GRC, and AI security advisory to mid-market and enterprise clients. It closely mirrors Sidekick's verticalized healthcare/financial practice mix.
• Coalfire: Coalfire is a leading cybersecurity advisory firm specializing in FedRAMP, HITRUST, SOC 2, and PCI compliance assessments plus advisory. It directly overlaps with Sidekick's Program Transformation and Government/Healthcare compliance offerings.
• Schellman Compliance: Schellman is a leading top-50 CPA firm specializing in cybersecurity assessments (SOC 2, ISO 27001, HITRUST, FedRAMP) with an emerging AI-security practice. It competes directly with Sidekick's Program Transformation and Healthcare/Government compliance offerings.
• Bishop Fox: Bishop Fox is a long-standing offensive-security pure-play offering penetration testing, red teaming, and attack-surface management to enterprise clients. It is closely comparable to Sidekick's Offensive Security pillar and shares the practitioner-led, COSO-style boutique delivery model.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks6 records

Key highlights7 records

Customer concentration

• YouTubeyoutube.com/channel/UCTVAU1P28aDIbQ7ZW0KvSpQ
• LinkedInlinkedin.com/company/sidekick-security

Compliance5 records

Revenue estimate

Valuation estimate

Number of profiles

Profiles1 record

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Sidekick Security