What Simplicity Ops does

Simplicity Ops (legal name: Simplicity Operations Management) is a privately held, bootstrapped operation management consultancy founded in March 2020 by Kate Guillen and headquartered remotely out of Southern California. The firm specializes in CRM optimization for independent registered investment advisors (RIAs), with a near-exclusive focus on the Redtail CRM platform and a secondary presence in Wealthbox. Its core service is a structured 6-month engagement that transforms an underutilized CRM into an operational hub, covering five proprietary competencies: contact management, task management, calendar management, pipeline management, and account management. Supporting frameworks include the RIA Operating System, a Workflow Development Framework, a Contact Hierarchy & Style Guide Framework, a CRM Assessment Process, and a Monthly Keyword Client Review System.

The company monetizes through a tiered, professional-services model: a $3,000 one-time CRM assessment, a $6,600/month subscription-style implementation engagement (total $33K-$39.6K) delivered through weekly strategy calls, database cleanup, workflow development, and team coaching, plus post-engagement hourly retainer consulting. A freemium RIA Operating System course on Skool and an ecosystem of free downloadable resources serve as top-of-funnel lead generation. Target clients are independent RIAs in the $200M-$800M AUM range with 4-14 person teams, with named engagements spanning Federal Retirement Authority, Ring Financial Services, Juno Financial Group, Yungreis Private Wealth, Hiley Hunt Wealth Management, Ballentine Capital Advisors, and at least a dozen additional advisory firms. Distribution is inbound-led through Kate Guillen's thought leadership (Kitces podcast, Advisor Talk with Frank Larosa, Advisorlab, Redtail webinars), the Skool-hosted RIA Operators Community, and referral partnerships with GReminders and Bento Engine (priced at $129/seat/month). The firm intentionally limits capacity to up to 10 client engagements per year through its 3-person team.

Name

Simplicity Ops

Legal name

Simplicity Ops

Website

https://simplicityoperations.com

Company type

Private

Founded year

2020

Operating status

Operating

Headcount range

1–10 employees

Short description

Simplicity Ops is a bootstrapped, founder-led consultancy that optimizes Redtail CRM and workflow systems for independent RIAs, serving $200M-$800M AUM advisory firms through fixed-fee assessments, 6-month implementation engagements, hourly retainers, and a self-paced course.

Ownership category

akta.pro rank

Headquarters

HQ city

San Diego

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2B

Offering type

Services

Cost components

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

Revenue model

1. CRM Assessment & Plan: Firms pay $3,000 for an initial CRM assessment and a custom implementation plan/roadmap. The plan is delivered as a written deliverable that firms can implement independently or hire Simplicity Ops for full implementation.
2. 6-Month Implementation Engagement: Billed monthly at $6,600/month for a 5–6 month deep-dive engagement. Includes weekly 1-hour strategy calls, contact database cleanup and organization, training on 5 core CRM competencies, workflow development, and team-wide coaching. Total engagement value approximately $33,000–$39,600.
3. Hourly/Retainer Consulting: Ongoing hourly consulting after the initial 6-month engagement. Firms can engage on an ad-hoc basis for workflow updates, new team member training, or operational brainstorming.
4. RIA Operating System™ Online Course: A self-paced online course available via Skool covering the RIA Operating System framework. Free overview course; premium access available for structured learning.

Pricing tiers

Go-to-market motion2 records

Distribution channels2 records

Marketing channels9 records

Core offering

Simplicity Ops is a specialized operations consultancy that helps independent registered investment advisors (RIAs) turn Redtail CRM into the centralized operational hub of their firms. The core deliverable is the proprietary RIA Operating System, which implements five competency areas (contact, task, calendar, pipeline, and account management) through paid CRM assessments, a 5–6 month hands-on implementation engagement with weekly coaching, custom workflow development, database cleanup, and team-wide training. Ongoing hourly consulting and a freemium online course on Skool extend the offering after the initial engagement.

Product overview

Simplicity Ops offers a unified RIA Operating System—a comprehensive CRM optimization and operational streamlining service for independent advisory firms. The core offering centers on implementing their five-component RIA Operating System within Redtail CRM, covering Contact Management, Task Management, Calendar Management, Pipeline Management, and Account Management. Their service portfolio includes CRM assessment, a 6-month implementation engagement with weekly coaching calls, workflow development, database cleanup, and ongoing hourly support. They provide free downloadable resources including Style Guides (for Redtail and Wealthbox), Redtail Tools Guide, and Billing Workflow Templates. The company also offers integration with Bento Engine, a partner fintech that provides age-based client milestone tracking through CRM APIs.

Differentiator

Problem solved

Functional benefit

Products and services

• CRM Optimization Services End-to-end optimization of Redtail CRM into a centralized operational hub for independent advisory firms, including database cleanup, contact organization, custom workflow development, and team-wide training. Intended for independent RIAs seeking operational consistency and scalability.
• CRM Assessment & Plan One-time fixed-fee ($3,000) diagnostic engagement involving data export analysis, identification of organizational gaps, and delivery of a prioritized written implementation roadmap that firms can execute independently or hand off to Simplicity Ops.
• 6-Month Implementation Engagement A 5–6 month deep-dive implementation engagement billed at $6,600/month (approximately $33,000–$39,600 total), including weekly 1-hour strategy calls, contact database cleanup and organization, training on five core CRM competencies, custom workflow development, and team-wide coaching.
• Ongoing Hourly Consulting Hourly consulting available after the initial 6-month engagement for workflow updates, new team member training, and operational brainstorming on an ad-hoc basis.
• RIA Operating System Course A self-paced online course delivered via Skool that teaches the proprietary RIA Operating System framework covering the five core competencies (contact, task, calendar, pipeline, account management) within Redtail CRM. Free overview tier with premium access for structured learning.
• Complimentary Growth Strategy Call A free initial consultation used to assess whether a firm's operating model is ready to support its next stage of growth and to determine fit for a paid engagement. Scheduled via the website and GReminders integration.

Quantifiable outcome

• Transition from 'digital rolodex' to streamlined service model: significantly improved firm efficiency (Juno Financial Group testimonial)
• +3 more outcomes

Named customers19 records

Segments2 records

Ideal customer profiles2 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration5 records

Feature5 records

Partnerships

Three partnerships are on record, tiered core and minor.

• Bento EnginecoreTechnology or IntegrationBento Engine is a fintech focused on wealth management client engagement. The platform tracks ages of contacts in the CRM and creates automated activities when clients/prospects reach certain age milestones (e.g., notifying advisors to discuss retirement catch-up contributions before a client's 50th birthday). Bento Engine integrates via APIs into CRMs to identify 'Next Best Actions' and provides compliance pre-approved content for advisors. Simplicity Ops recommends and implements Bento Engine as part of its CRM optimization engagements. Bento Engine pricing starts at $129/seat/month.
• Redtail TechnologycoreTechnology or IntegrationRedtail Technology is the primary CRM platform Simplicity Ops specializes in. Kate Guillen is a recognized Redtail expert who has invested years training with Redtail's training team. Simplicity Ops is featured as a guest expert on Redtail's own webinar platform (Practice Management Takeover), and Redtail's help desk hosts Simplicity Ops's downloadable resources. The partnership is central to Simplicity Ops's service offering.
• RIA Operators Community (Skool)minorGTM or Marketing PartnerAn external community platform on Skool where RIA operators share best practices. Simplicity Ops directs clients and prospects to this community as a resource. Kate Guillen is active in this community, using it as an ongoing engagement channel and referral source.

Scale indicators4 records

Recent moves6 records

Expansion highlights5 records

Direct peers

• Elite Consulting Partners: Consulting firm specializing in business development, talent placement, and operational consulting for RIAs. Directly comparable to Simplicity Ops as an advisory-firm consultancy; Elite is even referenced in Simplicity Ops's own podcast appearances (Advisor Talk with Frank LaRosa).
• RIA in a Box: Compliance and operations consulting/services firm for registered investment advisors. Comparable in serving the operational and regulatory infrastructure needs of independent RIAs with a similar consulting-led model.
• FP Transitions: Consulting and M&A advisory firm serving RIAs and financial advisors on transitions, valuations, and practice management. Comparable professional services firm addressing operational and growth challenges for the same RIA customer base.
• CEG Worldwide: Coaching, consulting, and research firm serving financial advisors on practice management and growth. Comparable as a consultancy operating in the same RIA coaching/operations niche with similar premium engagement models.

Broad incumbents

• Redtail Technology: CRM platform vendor for financial advisors that Simplicity Ops builds upon. Directly related as the technology foundation of Simplicity Ops's services; Redtail's distribution scale and product roadmap directly affect Simplicity Ops's addressable market.
• Wealthbox: CRM platform purpose-built for financial advisors and a direct alternative to Redtail. Comparable as the second CRM Simplicity Ops supports with Style Guides, representing both a competitor ecosystem and a potential horizontal expansion target.
• Carson Group: Large RIA support services firm offering consulting, coaching, technology, and back-office services to independent advisors. Comparable as a much larger incumbent offering operational enablement for RIAs, with bundled services that overlap Simplicity Ops's offering.
• Orion Advisor Solutions: Large wealth-technology platform offering CRM, portfolio accounting, and advisor technology. Comparable as a broad incumbent in the advisor technology stack; potential acquirer of specialized implementation partners like Simplicity Ops.

Emerging players

• Practifi: CRM and practice management platform for financial advisors competing directly with Redtail and Wealthbox. Comparable as an alternative CRM platform whose adoption could either expand or threaten Simplicity Ops's addressable market.

Others

• Nitrogen (formerly Riskalyze): Risk-profiling and proposal software for financial advisors integrated into the CRM workflow. Comparable as an adjacent technology that integrates with Redtail and complements Simplicity Ops's optimization stack for advisory firms.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Customer concentration

• LinkedInlinkedin.com/company/simplicity-ops

Revenue estimate

Valuation estimate

Number of profiles

Profiles4 records

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 Simplicity Ops