Full-Time

Client Experience Lead

Posted on 1/6/2026

Thoughtful

Thoughtful

51-200 employees

Automates repetitive business processes with modules

No salary listed

Austin, TX, USA

In Person

Category
Operations & Logistics (1)
Required Skills
Risk Management
Data Analysis
Requirements
  • Demonstrated experience leading complex, multi-workstream programs that require coordination across engineering, data/analytics, operations, and customer teams.
  • 5+ years in a customer-facing delivery, program management, or consulting role, with proven ability to guide organizations through operational or technology transformation.
  • Strong ability to bring clarity to ambiguity, align decision-makers, and drive structured, high-quality decision-making across diverse stakeholders.
  • Experience translating business or operational workflows into technology-enabled solutions, including validating key design decisions with technical teams.
  • Exceptional written and verbal communication skills, with the ability to articulate expectations, decisions, and outcomes to executives.
  • Strength in early risk identification, issue resolution, and maintaining overall program health to ensure successful deployments.
  • Strong prioritization and problem-solving skills; able to simplify complexity and guide teams toward measurable outcomes.
  • Entrepreneurial mindset with the determination to remove obstacles and deliver high-quality results.
Responsibilities
  • Accountable for the successful delivery of Smarter Technology solutions and driving transformation at our most critical customer partners.
  • Deploy delivery strategy, governance structures, milestones, and resource plans across complex, multi workstream programs.
  • Provide clear, structured, and actionable communications to both Smarter Technology and customer executives.
  • Drive, direct, coach, and support cross-functional teams, modeling structured, thoughtful decision-making.
  • Contribute to delivery playbooks, standards, and methodologies that improve consistency and scale.
  • Lead customers through AI-driven RCM and HITL implementations, ensuring clarity of workflows, decisions, expectations, and operational outcomes.
  • Help customers understand what is being built, why it matters, and how it will deliver measurable impact.
  • Bring clarity to ambiguous situations and align stakeholders and decision-makers across customer organizations.
  • Partner with technical teams to translate customer workflows into accurate, scalable AI and HITL processes, and validate key design decisions.
  • Orchestrate engineering, TPM, data, operations, and customer teams to maintain alignment and execution.
  • Support overall program health by maintaining visibility into deployment progress, risks, and dependencies, identifying issues early and coordinating resolution to keep the program on track.
  • Ensure each deployment achieves the customer’s defined goals and delivers improvements aligned with the outcomes set at the start of the partnership.
  • Identify opportunities to strengthen performance and coordinate with Customer Success on any potential expansion discussions across the customer organization.
  • Build confidence and long-term partnership success by ensuring high-quality delivery and sustained operational impact.
Desired Qualifications
  • Experience in Revenue Cycle Management (RCM) operations, transformation, or technology enterprise implementation.
  • Familiarity with HITL systems, AI-driven automation, or healthcare workflow technologies.
  • Background working with healthcare provider groups, payers, or RCM service organizations.

Thoughtful Automation provides automation modules that perform repetitive business tasks to help companies streamline operations and reduce costs. The modules are software components that can be deployed across various business processes, such as billing and compliance, and run tasks automatically to free up staff for higher-value work. Unlike some competitors that may offer generic software, Thoughtful Automation uses a service-based model and sells modular automation solutions that are easy to deploy across different processes, making automation affordable and scalable. The company’s goal is to help businesses save time and money, improve productivity, and enable teams to focus on strategic tasks.

Company Size

51-200

Company Stage

Series A

Total Funding

$35.8M

Headquarters

Chicago, Illinois

Founded

2020

Simplify Jobs

Simplify's Take

What believers are saying

  • Smarter Technologies combination leverages $800M revenue and 200+ clients.
  • Reduces claim denials by 75% and operational costs by 80%.
  • Acquisition by New Mountain Capital accelerates AI scaling in healthcare.

What critics are saying

  • Smarter Technologies integration dilutes Thoughtful's RCM brand focus.
  • Jeremy Delinsky's oversight burdens startup agility with 60 hospitals.
  • Athenahealth's marketplace competes directly, eroding partnerships.

What makes Thoughtful unique

  • Thoughtful AI deploys specialized agents EVA, PAULA, CODY, CAM, DAN, PHIL for RCM tasks.
  • Integrates NLP, OCR, LLMs into existing EHRs and athenahealth Marketplace.
  • Performance-based pricing charges only for RCM efficiency improvements.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Paid Vacation

Stock Options

Growth & Insights and Company News

Headcount

6 month growth

30%

1 year growth

34%

2 year growth

27%
Yahoo Finance
May 20th, 2025
New Mountain Combines Three Companies To Create Smarter Technologies

Investment firm New Mountain Capital has merged three portfolio companies SmarterDx, Thoughtful.ai and Access Healthcare for the formation of Smarter Technologies. The integrated capabilities of the new healthcare efficiency automation platform is poised to enhance revenue management, operational workflows, and strengthen financial performance. New Mountain Capital Private Equity managing director and president Matt Holt said: “We identified the market leaders across the most important areas of agentic-AI, machine learning and clinical data, and large-scale automation in the three companies and are now combining them to create the innovation leader of the sector. “We see enormous potential for growth and an opportunity to transform the industry.” Smarter Technologies caters to over 60 hospitals and health systems, as well as more than 500,000 providers. The company handles over 400 million transactions and oversees upwards of $200bn in collective annual revenue. SmarterDx, founded in 2020, specialises in clinical AI for care quality and revenue integrity

Business Wire
Apr 11th, 2025
Thoughtful.ai Announces Growth Investment from New Mountain Capital

Thoughtful Automation Inc. (“Thoughtful.ai”), a leading artificial intelligence (AI)-powered revenue cycle automation company, today announced a strategic in...

myMotherLode.com
Apr 10th, 2025
Thoughtful.ai Gains Investment from New Mountain

Thoughtful.ai, an AI-powered revenue cycle automation company, announced a strategic investment from New Mountain Capital, a firm with over $55 billion in assets under management. This investment aims to accelerate AI adoption in healthcare revenue cycle management, enhancing efficiency and patient care. The transaction is pending regulatory approval and is expected to close in Q2.

PYMNTS
Nov 3rd, 2024
Nvidia Reportedly Weighing Investment In Musk’S Xai

Nvidia is in discussions to invest in Elon Musk’s artificial intelligence (AI) startup, according to published reports. Musk’s AI firm xAI is hoping to raise several billion dollars, valuing the company at around $40 billion, the New York Post reported Friday (Nov. 1). A separate report by The Information says Musk had been in discussions with tech companies and venture firms such as Sequoia Capital, Andreessen Horowitz and Vy Capital

PYMNTS
Oct 27th, 2024
Report: Google Exploring Ai That Can Take Over Web Browsers

Google is reportedly developing an artificial intelligence (AI) technology that can take over web browsers.The tech giant plans to show off this AI product — which carries the codename “Project Jarvis” — as soon as December, when it rolls out its next Gemini large language model, The Information reported Saturday (Oct. 26).OpenAI is working on an AI model that could conduct research by browsing the web autonomously with the help of a computer-using agent, or CUA, that can take actions based on its findings.However, the report said, Google would take the concept further with software that can directly interact with a user’s browser.PYMNTS has contacted Google for comment but has not yet received a reply.The news comes days after AI company Anthropic launched a new capability dubbed “computer use” that lets its AI interact with users’ computer screens.As reported here, this tool allows Anthropic’s AI to interpret on-screen content and, with user consent, carry out tasks such as web browsing, button clicking and text input.“This development marks a shift in AI assistance technology, as it can process real-time screen activity rather than relying on back-end application integrations,” PYMNTS wrote.In a demonstration, the system showed off its abilities by planning a morning hike near the Golden Gate Bridge, autonomously seeking out trails, checking sunrise times and creating calendar invites with detailed info about proper hiking attire.“The release comes amid growing industry interest in AI agents that can operate with minimal human oversight,” PYMNTS wrote. “While companies like Microsoft and Salesforce have recently introduced their agent tools for workplace tasks, Anthropic’s approach differs in that it focuses on direct screen interpretation rather than application-specific integration.”And as argued here in a separate report, Anthropic’s move puts the company in direct competition with the likes of Google and Microsoft, which are attempting to automate routine computer tasks for businesses looking to increase productivity and reduce costs.While past AI tools have focused on text and image generation, these new agents mark an evolution toward AI systems that can actively manipulate software and carry out complex workflows with human oversight kept to a minimum.“Agentic AI is set to redefine industries over the next three years, with its ability to operate autonomously and make decisions without human intervention,” Dan Parsons, COO/CPO at Thoughtful AI, told PYMNTS.“The greatest impact will be seen in areas like system administration, operations, customer service, and complex decision-making, where AI can drastically improve efficiency, reduce costs, and unlock new levels of scalability.”For all PYMNTS AI coverage, subscribe to the daily AI Newsletter

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