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Red Oak

Automated compliance workflow for financial advertising

GTM Systems Administrator

Full-TimeUpdated on 10/23/2026
No salary listed
Mid
Austin, TX, USA
HybridHybrid in Austin with a minimum of 3 office days each week, Tuesday through Thursday.
IT OperationsEnterprise Applications

About the job

Requirements
  • Expertise administering Salesforce.
  • Experience owning more than one component of the go-to-market stack.
  • A background in software as a service.
  • Ability to work quickly across simultaneous stakeholder requests and exercise independent judgment.
  • Ability to build AI agents and automations, not only use existing AI tools.
Responsibilities
  • Administer both Salesforce instances through the merger and own the consolidated Salesforce organization afterward, including user setup, permissions, workflows, and integrations.
  • Diagnose Salesforce data-quality issues at their root cause and create safeguards against recurring problems.
  • Partner with Marketing Operations on marketing-to-sales handoffs and pipeline metrics, and with Sales Operations on data hygiene supporting its analysis.
  • Understand the HubSpot connector and broader go-to-market tools sufficiently to work across the stack; Marketing Operations owns HubSpot itself.
  • Create and maintain training materials when changing processes or tools that users rely on.
  • Use AI daily in personal workflows, execute recommendations from existing Claude agents, and build agents and additional automation as integrations become available.
Desired Qualifications
  • A financial services background.
  • Experience with post-merger or mergers-and-acquisitions systems integration.

About the company

Red Oak Compliance provides compliance software and services to financial services and insurance firms. Its main product is a SaaS platform that automates the submission, review, and approval of advertising and marketing materials to ensure they comply with regulations from bodies like the SEC and FINRA, and to preserve electronic records in line with SEC Rule 17a-4. The offering combines software with consulting services, giving clients both the automated workflow and regulatory guidance. The company differentiates itself by delivering an integrated solution that covers end-to-end compliance workflows for advertising materials and related risk management, rather than just generic software. Its goal is to help broker-dealers, investment advisers, and insurance companies meet regulatory obligations efficiently and reduce compliance risk by acting as a comprehensive compliance partner.

Company Size

51-200

Company Stage

Growth Equity (Venture Capital)

Total Funding

$51M

Headquarters

Cedar Park, Texas

Founded

2010

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Simplify's Take

What believers are saying

  • The July 2026 merger creates cross-sell into MirrorWeb capture customers immediately.
  • Red Oak's July 13, 2026 connector automates approvals into 4U, shrinking manual workflow friction.
  • Hiring continued in 2026, with headcount rising to 138 and new product leadership added.

What critics are saying

  • Romir Bosu's July 2026 integration must unify two stacks without customer disruption by 2027.
  • Smarsh launched AI supervision upgrades in May 2026, pressuring Red Oak's pricing and renewal power.
  • A single archiving or supervision failure triggers SEC or FINRA enforcement and existential customer flight.

What makes Red Oak unique

  • Red Oak and MirrorWeb merged July 28, 2026, spanning creation through archiving.
  • Its platform links ad review, distribution, supervision, and regulated communications in one audit trail.
  • It serves 1,550-plus regulated firms, including 17 of the top 20 asset managers.

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Benefits

  • Equity Units
  • Healthcare Insurance
  • 5% 401K match
  • Unlimited PTO

Growth & Insights and Company News

6 month growth

0%

1 year growth

5%

2 year growth

11%
Citybiz
Jul 28th, 2026
Red Oak and MirrorWeb merge to create unified compliance platform serving 17 of world's 20 largest asset managers

Red Oak and MirrorWeb have agreed to merge their compliance technology platforms, creating an integrated solution for managing regulated communications across financial services. Financial terms were not disclosed. The combined platform will span content creation, compliance review, distribution, communications supervision, and regulatory archiving. MirrorWeb CEO Romir Bosu will lead the merged entity, which operates under the Red Oak brand. The companies serve 17 of the world's 20 largest asset managers, collectively representing over $62 trillion in assets under management, alongside more than 1,550 regulated firms. Red Oak's platform handles marketing content creation and AI-assisted regulatory approvals. MirrorWeb provides communications capture and supervision across channels including email, WhatsApp, and LinkedIn, using its Mira AI engine to identify conduct risks. The merger addresses growing demand for unified compliance systems as financial institutions face expanding digital communications volumes and increasingly complex regulatory requirements.

PR Newswire
Feb 9th, 2026
Red Oak appoints Kirk Sadler as chief product officer to drive compliance platform growth

Red Oak, a compliance connectivity platform for financial services, has appointed Kirk Sadler as chief product officer. Sadler will work across engineering, sales, marketing and leadership teams to drive product roadmap priorities and return on investment for clients. Sadler brings over 20 years of product management experience in B2B enterprise software, including leading organisations through six acquisitions. He previously spent nearly a decade as vice president of product at Mitratech, where he built solutions for legal, risk and compliance professionals across Global 1000 companies in regulated industries. Red Oak's platform connects content creation, review, distribution and supervision for financial services firms, powered by what it calls Compliance-Grade AI. The company aims to streamline marketing content approvals whilst enabling distribution and analytics.

PR Newswire
Jan 20th, 2026
Red Oak appoints Michael Allain as chief revenue officer with 30 years' B2B sales experience

Red Oak, a compliance connectivity platform for financial services, has appointed Michael Allain as Chief Revenue Officer. Allain will lead revenue growth initiatives and work across sales, operations and leadership teams. Allain brings over 30 years of B2B sales experience, including more than two decades in financial services. He previously served as Executive Vice President of Sales at Billd and Vice President of Sales at Rho, and spent over 15 years at American Express leading regional sales organisations. Red Oak provides a platform that integrates content creation, review, distribution and supervision for financial services firms. The company uses compliance-grade AI to streamline marketing content workflows and enable distribution through its 4U system.

Ellis County Press
Jul 30th, 2025
Red Oak holds first annual Sweat Out Cancer 5K Fun Run and Walk

Red Oak holds first annual Sweat Out Cancer 5K Fun Run and Walk.

Red Oak
May 9th, 2025
Branching Out, Deepening Roots, and Expanding Horizons: Highlights from the 2025 Red Oak User Conference

Red Oak Compliance just wrapped its 6th Annual Red Oak User Conference in Austin, and Red Oak Compliance is still energized by the community, conversations, and breakthroughs that filled the room.