OnTrajectory

What OnTrajectory does

OnTrajectory is a privately held, US-based financial planning software company founded in 2014 by Tyson Koska, with Linda Bready serving as President. The company operates from Lutherville Timonium, Maryland, with a small core team of 1-10 employees supplemented by a seven-person engineering group based in Ukraine, and serves a user base of 2,263+ individuals and an undisclosed number of financial professionals.

The company offers a cloud-based financial planning platform built around Monte Carlo simulations, historical analysis, scenario comparison, and tax optimization, deployed through three core products: OnTrajectory Goals (collaborative, entry-level planning for consumers), OnTrajectory Cashflow (professional-grade cash flow modeling with account management, tax bracket analysis, and debt-reduction strategies), and ProPortal (a B2B workspace for financial advisors managing up to 25 clients with custom-branded PDF reports). Supplementary offerings include the Advisor Affiliate Program for lead generation, Penny (an AI Financial Guide delivering conversational text responses), Ask an Advisor (a referral service to licensed professionals), One-to-One Data Review sessions, and structured masterclasses plus a Financial Modeling course on a dedicated learning domain.

OnTrajectory monetizes primarily through subscriptions: a free Basic tier and an Unlimited consumer plan at $80/year or $9/month; ProPortal at $69/month for advisors; and the Advisor Affiliate Program at $99/month. Ancillary revenue comes from $200/60-minute data review sessions and educational programs. Distribution is predominantly self-serve and product-led growth via direct website registration, augmented by community-led engagement (Facebook group, weekly Office Hours, YouTube) and an affiliate channel through independent financial advisors, with no disclosed external funding.

Name

OnTrajectory

Legal name

OnTrajectory

Website

https://ontrajectory.com

Company type

Private

Founded year

2014

Operating status

Operating

Headcount range

1–10 employees

Short description

OnTrajectory is a bootstrapped, US-based financial planning software company that offers Monte Carlo simulation-driven goal and cash flow planning tools to individual consumers and financial advisors via freemium and subscription tiers.

Ownership category

akta.pro rank

Product category

Personal Financial Planning Software

SIC

Services-Prepackaged Software (7372), Investment Advice (6282)

akta.pro primary industry

Automated Rebalancing, Tax-Loss Harvesting & Tax-Optimized Investing Tools (FSAGAEAE)

Keywords

• Financial planning software
• Retirement planning tools
• Monte Carlo simulation
• Cash flow modeling
• Goals-based planning

Headquarters

HQ city

Lutherville Timonium

HQ country

United States

HQ region

North America

Markets served

GTM type

B2B and B2C

Offering type

Software

Cost components

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

Revenue model

1. Subscription - Unlimited Plan: Premium subscription at $80/year or $9/month offering unlimited scenarios, Monte Carlo analysis, tax optimization, and advanced features
2. Advisor Affiliate Program: Monthly subscription for financial advisors to access lead generation and nurturing tools, $99/month for up to 100 leads
3. ProPortal Professional Tools: Monthly subscription at $69/month for financial professionals with up to 25 clients, includes onboarding and support
4. One-to-One Data Review Services: Personalized guidance sessions at $200 for 60 minutes, with follow-up sessions at $100 for 30 minutes
5. Masterclass and Courses: Educational programs including Financial Modeling course powered by OnTrajectory

Pricing tiers

Go-to-market motion5 records

Distribution channels5 records

Marketing channels7 records

Core offering

OnTrajectory is a cloud-based financial planning software platform that enables individuals and financial professionals to build lifetime financial models, run Monte Carlo and historical simulations, compare multiple scenarios, and perform tax optimization. It offers two main consumer products—OnTrajectory Goals (collaborative, goal-based planning) and OnTrajectory Cashflow (professional-grade cash flow planning)—along with the ProPortal for independent financial advisors to manage and collaborate with clients.

Product overview

OnTrajectory is a financial planning software platform offering multiple integrated products: OnTrajectory Goals provides goals-based planning for individuals, while OnTrajectory Cashflow offers comprehensive cash flow modeling for advanced users. The ProPortal serves financial professionals with client management tools. Additional offerings include Ask an Advisor (access to licensed professionals), the Advisor Affiliate Program for lead generation, One-to-One Data Review Services, Masterclass training, and the Financial Modeling course. The platform also includes Penny, an AI Financial Guide, and offers Office Hours for community support. The Basic tier is free with essential features, while Unlimited ($80/year or $9/month) and ProPortal ($69/month) provide advanced capabilities including Monte Carlo analysis, historical simulations, and tax optimization.

Differentiator

Problem solved

Functional benefit

Brands

• OnTrajectory Goals: Goals-based planning tool for collaborative financial planning
• OnTrajectory Cashflow
• ProPortal
• Penny
• Advisor Affiliate Program

Products and services

• OnTrajectory Goals A collaborative, goals-based financial planning tool designed for individuals who want to grow their financial knowledge, build long-term plans (retirement, college, home purchase), and visualize outcomes over 30-50 years with real-time scenario updates.
• OnTrajectory Cashflow A cash flow planning tool offering account management, tax optimization, debt reduction strategies, and customizable chart settings for smart budgeters and users with complex account structures who want a clear picture of where their money is going.
• ProPortal A professional portal for independent financial advisors to collaborate side-by-side with up to 25 clients in real time, including real-time updating charts, advanced analysis tools, custom branding on PDF reports, and onboarding support.
• Ask an Advisor A service that connects OnTrajectory users with licensed financial advisors for questions and second opinions on financial matters, with no commitment or obligation.
• Advisor Affiliate Program A program that enables financial advisors to run marketing campaigns with goal-based planning tools, generate and qualify leads through custom OnTrajectory links, and nurture prospects before initial consultation.
• One-to-One Data Review Services Personalized guidance sessions where an OnTrajectory expert provides live screen-sharing support to help users craft their financial plan, including reviewing income streams, creating budget groups, and running simulations.
• Masterclass Options Cohort-based training programs that teach users how to use OnTrajectory to model their financial future, available through the learn.ontrajectory.com platform.
• Financial Modeling Course A course teaching critical financial aspects for mapping one's financial future, powered by OnTrajectory, covering key concepts and levers to minimize effects of financial unknowns.

Quantifiable outcome

• Users report successful early retirement decisions supported by OnTrajectory analysis
• +1 more outcomes

Named customers6 records

Segments3 records

Ideal customer profiles2 records

Technology focussed Yes

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

AI capability2 records

Feature9 records

Scale indicators3 records

Recent moves6 records

Expansion highlights5 records

Direct peers

• Empower (formerly Personal Capital): Direct competitor offering personal financial management dashboards, retirement planning with Monte Carlo simulations, and a hybrid model combining free tools with human advisor services. Closely aligned with OnTrajectory's consumer+advisor dual-product strategy, but at much greater scale and with substantial outside capital.
• NewRetirement: Direct peer in the DIY retirement planning space, offering Monte Carlo simulations, scenario modeling, tax optimization, and an advisor referral marketplace. Highly comparable in product scope and target audience (mass-affluent self-directed planners and advisors).
• RightCapital: Financial planning software purpose-built for financial advisors, with goal-based planning, tax planning, and Monte Carlo analysis. Directly competes with OnTrajectory's ProPortal offering for the same independent advisor customer segment.
• eMoney Advisor: Advisor-focused financial planning platform owned by Fidelity, offering comprehensive cash flow, retirement, tax, and estate planning tools. Competes with OnTrajectory's ProPortal for enterprise and mid-market advisor accounts.
• MoneyGuidePro: Long-established financial planning platform for advisors with goal-based planning, Monte Carlo simulations, and tax-efficient withdrawal strategies. Direct competitor in the ProPortal/affiliate addressable market with deep advisor market penetration.
• YNAB (You Need A Budget): Subscription-based personal budgeting and financial planning software targeting consumers with a goal-based, education-rich approach. Comparable in PLG motion and consumer subscription pricing tier, though focused more on budgeting than long-horizon retirement modeling.
• Monarch Money: Modern consumer subscription financial planning platform with collaborative features, scenario planning, and account aggregation. Targets a similar self-directed planning audience as OnTrajectory Goals and Cashflow, with overlapping feature sets and PLG distribution.
• Boldin (formerly NewRetirement's advisor suite): Financial planning software for both consumers and advisors, with retirement income, tax, and estate planning modules. Direct overlap with OnTrajectory's combined consumer/advisor strategy and Monte Carlo-based planning capabilities.

Emerging players

• ProjectionLab: Subscription-based personal financial projection tool focused on FIRE (financial independence, retire early) planning with detailed cash flow and net worth forecasting. Niche overlap with OnTrajectory in the FIRE/early-retirement community that OnTrajectory also targets.

Broad incumbents

• Intuit Credit Karma (formerly Mint): Free consumer budgeting and financial tracking tool backed by Intuit, with massive user base and broad financial product marketplace. Competes at the free-tier level, limiting OnTrajectory's conversion funnel from price-sensitive consumers.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks6 records

Key highlights6 records

Customer concentration

• YouTubeyoutube.com/@ontrajectory
• Facebookfacebook.com/508862169217440
• Xx.com/ontrajectory

Revenue estimate

Valuation estimate

Number of profiles

Profiles2 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 OnTrajectory