Strategic AI Consultation by Josh PitzalisStrategic AI Consultation by Josh Pitzalis
Strategic AI ConsultationJosh Pitzalis
Cover image for Strategic AI Consultation
Unlike generic AI consulting that gives you theoretical advice, I focus on practical, implementable solutions tailored to your specific technical constraints and business goals. You get clarity on whether to build new features, fix existing ones, or optimize your current approach - with concrete next steps and timelines rather than vague recommendations.
What makes this unique: Most AI consultants either sell you their preferred solution or give abstract advice, but I provide unbiased, practical guidance based on your actual situation and constraints, helping you make confident decisions before committing significant development resources.

What's included

Strategic Discussion Recording
A comprehensive 2-hour video call where we dive deep into your AI product challenges, explore potential solutions, and align on the best path forward. This isn't just a presentation of findings - it's an interactive strategy session where you can ask questions, challenge assumptions, and work through implementation concerns in real-time. You'll get the recording to share with your team and reference later as you execute on the recommendations.
Discussion Transcript
A complete transcript of our 2-hour strategy session, cleaned up and organized for easy reference. This ensures you have a written record of all recommendations, action items, and key insights discussed, making it easy to share with team members who weren't on the call and reference specific points as you implement the suggested changes.
Follow-up Research & Resources
A curated collection of links, tools, frameworks, and references based on everything we discussed during our session. I spend 2 hours after our call researching and compiling the specific resources, documentation, and implementation guides that relate to your unique situation, giving you a head start on executing any of the strategies or solutions we explored together.
FAQs
I'm Josh Pitzalis, working alongside my development partner Sasha Koss. Together we built Chirr App, one of the first Twitter thread schedulers back in 2017, and have over 15 years of combined development experience. Sasha is the author of date-fns, the second most popular JavaScript utility library in the world according to the 2024 State of JS report. We've been exploring AI infrastructure and evaluation systems through projects like Mind Control (a CMS for production AI prompts) and DaisyChain (a no-code prompt chaining tool). Our backgrounds combine deep software engineering expertise with an understanding of the LLM evaluation process and practical lessons form building two AI-infrastructure projects.
- 2 hours of your time. - You can share access to your AI systems and current performance data over the call if you want it to be reviewed, but these is no expectation to.
For the development and evaluation services we offer, we tend to focus on growth-stage companies (Series A-C) with established AI products and meaningful API spending ($5K+ monthly). However, the consultation service is designed for any stage company that needs strategic clarity on their AI approach - whether you're pre-Series A exploring AI possibilities or a larger company deciding between different implementation paths.
Perfect - that's exactly what I specialize in. Generic monitoring tools and cookie-cutter solutions fail because every AI application has unique failure modes and requirements. I generally work with you to create custom evaluation frameworks and development approaches that understand your specific domain, whether that's legal document analysis, medical diagnosis, financial risk assessment, or something completely different.
All development work is done in TypeScript, which integrates well with most modern web applications. For evaluation services, I work with your existing infrastructure regardless of language - the monitoring and evaluation systems are designed to work alongside your current setup.
I work within your existing security protocols and can sign NDAs as needed. For sensitive data, we can work with synthetic data or implement evaluation systems that don't require exposing actual customer data. All code and documentation developed during our engagement belongs entirely to you.
Yes, I have experience working with companies in legal, healthcare, and financial services. I understand the additional compliance requirements and can help design evaluation systems that meet regulatory standards while still providing actionable insights.
All services include built-in buffer time, but if scope changes significantly, we'll discuss timeline adjustments upfront. The goal is always to deliver complete, working solutions within the stated timeframe.
All services include a 90-day support period for questions and adjustments. For longer-term support or additional features, we can discuss a follow-up engagement.
For the consultation service, if you don't find the session valuable you'll get a full refund. I'll only charge you if you genuinely found the consultation useful to your situation. Since AI development is still such an early-stage field with everyone doing things differently, there's a strong chance our experience can help based on the problems we've solved before, but if we can't add value to your specific situation, then we don't charge you - it's that simple. For the development and evaluation services, all engagements include a satisfaction guarantee. If you don't see measurable improvement or deliverables that meet the agreed specifications, we'll work together to make it right or provide appropriate compensation.
Starting at$500
Schedule a call
Duration1 day
Tags
Dovetail
Zoom
AI Engineer
Engineering Manager
Product Manager
Service provided by
Strategic AI ConsultationJosh Pitzalis
Starting at$500
Schedule a call
Duration1 day
Tags
Dovetail
Zoom
AI Engineer
Engineering Manager
Product Manager
Cover image for Strategic AI Consultation
Unlike generic AI consulting that gives you theoretical advice, I focus on practical, implementable solutions tailored to your specific technical constraints and business goals. You get clarity on whether to build new features, fix existing ones, or optimize your current approach - with concrete next steps and timelines rather than vague recommendations.
What makes this unique: Most AI consultants either sell you their preferred solution or give abstract advice, but I provide unbiased, practical guidance based on your actual situation and constraints, helping you make confident decisions before committing significant development resources.

What's included

Strategic Discussion Recording
A comprehensive 2-hour video call where we dive deep into your AI product challenges, explore potential solutions, and align on the best path forward. This isn't just a presentation of findings - it's an interactive strategy session where you can ask questions, challenge assumptions, and work through implementation concerns in real-time. You'll get the recording to share with your team and reference later as you execute on the recommendations.
Discussion Transcript
A complete transcript of our 2-hour strategy session, cleaned up and organized for easy reference. This ensures you have a written record of all recommendations, action items, and key insights discussed, making it easy to share with team members who weren't on the call and reference specific points as you implement the suggested changes.
Follow-up Research & Resources
A curated collection of links, tools, frameworks, and references based on everything we discussed during our session. I spend 2 hours after our call researching and compiling the specific resources, documentation, and implementation guides that relate to your unique situation, giving you a head start on executing any of the strategies or solutions we explored together.
FAQs
I'm Josh Pitzalis, working alongside my development partner Sasha Koss. Together we built Chirr App, one of the first Twitter thread schedulers back in 2017, and have over 15 years of combined development experience. Sasha is the author of date-fns, the second most popular JavaScript utility library in the world according to the 2024 State of JS report. We've been exploring AI infrastructure and evaluation systems through projects like Mind Control (a CMS for production AI prompts) and DaisyChain (a no-code prompt chaining tool). Our backgrounds combine deep software engineering expertise with an understanding of the LLM evaluation process and practical lessons form building two AI-infrastructure projects.
- 2 hours of your time. - You can share access to your AI systems and current performance data over the call if you want it to be reviewed, but these is no expectation to.
For the development and evaluation services we offer, we tend to focus on growth-stage companies (Series A-C) with established AI products and meaningful API spending ($5K+ monthly). However, the consultation service is designed for any stage company that needs strategic clarity on their AI approach - whether you're pre-Series A exploring AI possibilities or a larger company deciding between different implementation paths.
Perfect - that's exactly what I specialize in. Generic monitoring tools and cookie-cutter solutions fail because every AI application has unique failure modes and requirements. I generally work with you to create custom evaluation frameworks and development approaches that understand your specific domain, whether that's legal document analysis, medical diagnosis, financial risk assessment, or something completely different.
All development work is done in TypeScript, which integrates well with most modern web applications. For evaluation services, I work with your existing infrastructure regardless of language - the monitoring and evaluation systems are designed to work alongside your current setup.
I work within your existing security protocols and can sign NDAs as needed. For sensitive data, we can work with synthetic data or implement evaluation systems that don't require exposing actual customer data. All code and documentation developed during our engagement belongs entirely to you.
Yes, I have experience working with companies in legal, healthcare, and financial services. I understand the additional compliance requirements and can help design evaluation systems that meet regulatory standards while still providing actionable insights.
All services include built-in buffer time, but if scope changes significantly, we'll discuss timeline adjustments upfront. The goal is always to deliver complete, working solutions within the stated timeframe.
All services include a 90-day support period for questions and adjustments. For longer-term support or additional features, we can discuss a follow-up engagement.
For the consultation service, if you don't find the session valuable you'll get a full refund. I'll only charge you if you genuinely found the consultation useful to your situation. Since AI development is still such an early-stage field with everyone doing things differently, there's a strong chance our experience can help based on the problems we've solved before, but if we can't add value to your specific situation, then we don't charge you - it's that simple. For the development and evaluation services, all engagements include a satisfaction guarantee. If you don't see measurable improvement or deliverables that meet the agreed specifications, we'll work together to make it right or provide appropriate compensation.
$500