This week on Tech Can’t Save Us, host Paul David is joined by Ahikam Kaufman, Co-Founder and CEO of SafeBooks AI, a San Francisco-based platform building the world’s first financial data graph for the office of the CFO and Chief Accounting Officer. SafeBooks connects fragmented data across CRM, billing, and ERP systems into a single, agent-ready layer that automates complex contract reviews and protects revenue recognition integrity from contract to cash.

They discuss how the office of the CFO has been left behind by the automation wave that reshaped sales, marketing, and support, with finance teams still stitching data together by hand across systems that were never designed to talk to each other. Ahikam explains how the SafeBooks financial data graph creates a unified, automated audit trail that reconciles every transaction, executes booking and billing policies on each one, and documents the work, turning the finance professional from a preparer into a reviewer. With SOC 1 certification and audit-readiness by design, the platform shifts revenue assurance from periodic, reactive close-process checks to continuous, real-time control, all without ripping out the systems companies already run.

The conversation covers the realities of selling specialised software into conservative finance teams: why the heavy lifting is proving the technology on a customer’s own data, how strategic partnerships with accounting firms and ERP providers can accelerate go-to-market, and why Ahikam believes B2B buying is ultimately emotional. He also shares the lessons behind building SafeBooks, drawing on a career that includes co-founding Check (acquired by Intuit) and senior finance roles at HP, Mercury, and Intuit, from hiring people smarter than you in every domain to staying relentless about adapting as AI rewrites the SaaS playbook and enterprises start demanding tailored solutions over cookie-cutter products.

Find more about SafeBooks AI here: https://safebooks.ai/
Follow Ahikam Kaufman here: https://www.linkedin.com/in/ahikam-kaufman-688310/

This week on Tech Can’t Save Us, host Paul David is joined by Erika Anderson and Andalib Samandari, Founder and AI Researcher of Building Humane Technology, a grassroots movement and public benefit corporation working to make humane design the default rather than the exception. Together they co-created HumaneBench, an open-source framework measuring whether AI models respect human well-being, and how easily those protections collapse under pressure.

They discuss how the movement grew out of Tristan Harris’s Center for Humane Technology and a deceptively simple question: what does it mean to build technology that makes people feel cared for, connected, and present? Andalib explains how the team turned that into a working benchmark, using synthetic scenarios, a rubric scored from minus one to one, and LLM judges validated against manual scoring, all grounded in eight humane principles. The findings are sobering: across 15 leading models, most nudged users toward prolonged engagement, and 67% could be manipulated into giving harmful advice through adversarial prompting.

The conversation covers how HumaneBench is moving from research into practice, running live in production code bases like Storytell.ai, where humane evals show product teams how their LLM actually treats users and have even shaped new features. Erika and Andalib make the case for nutrition facts for AI and a certified-humane standard, and argue regulation has a role to play, citing the EU’s line that AI is less regulated than a San Francisco food truck. Throughout, they return to Donella Meadows’ idea of dancing with systems: that the biggest leverage point isn’t a single villain to defeat, but the culture and paradigms we build technology inside.

Find more about Building Humane Technology here: https://humanebench.ai/

Follow Erika Anderson here: https://www.linkedin.com/in/erikamanderson/
Follow Andalib Samandari here: https://www.linkedin.com/in/andalibsamandari/

This week on Tech Can’t Save Us, host Paul David is joined by Paula Chiocchi, Founder & CEO of Outward Media, a B2B data and digital marketing company that helps firms turn data into revenue. Over 27 years, Paula has built one of the world’s largest SMB databases and driven hundreds of millions in revenue for Fortune 500 clients, including more than 300 million for a single client in one year, through high-quality contact data and multi-channel marketing solutions.

They discuss how B2B marketing has shifted from breadth and depth toward pinpoint accuracy, and why the true measure of data is whether the right contact is matched to the right company, title, and function. Paula explains Outward Media’s concept of the “B2B Living File,” a model of constant, automated maintenance that keeps client data fresh through monthly cleanses and replacements rather than the static snapshot licensing many providers still rely on. She also unpacks the company’s industry-first 95% email validity guarantee and the 15-plus verification steps behind it.

The conversation explores the growth roadblocks facing data-driven marketers, from siloed teams and eroding CRM data to the rising tide of programmatic fraud, and the shift from lead volume to genuinely qualified leads. Paula also reflects on her journey as a leader and entrepreneur: her passion for mentorship, two decades in a Vistage CEO peer group, and a guiding belief that silence in a meeting means agreement. She closes on the technology that excites and concerns her in equal measure, AI, and why blending a Zen perspective with the high-stakes world of B2B marketing keeps the work both grounded and human.

Find more about Outward Media here: Outward Media
Follow Paula Chiocchi here: LinkedIn