Augment

Paddle appoints Jimmy Fitzgerald as president and COO
Truecaller unveils enterprise solutions for business
Upper90 raises $55M
Chili Piper raises Series B
Substack announces a $1M initiative to fund local journalists
UserZoom raises $100M,
MedChron LLC Launches Its Innovative New SaaS

Show Notes

Paddle, the Revenue Delivery Platform for B2B Software-as-a-Service (SaaS) companies appoints software industry veteran Jimmy Fitzgerald to the position of President and Chief Operating Officer. In his new role, Fitzgerald will help Paddle with its mission to supercharge the growth of fast-scaling software businesses everywhere. Fitzgerald was COO at SaaS price optimization startup SignalDemand (acquired by PROS) and held senior leadership positions at customer relationship management (CRM) pioneer Siebel Systems (later acquired by Oracle). Caller-identification application Truecaller announces a new solution for enterprises, which will allow businesses to verify their identity on the platform. With this feature, verified businesses will get a green caller ID and a verified business badge, and can also lock their brand name and profile photo. However, consumers will continue to see the number of spam markings as usual and they retain the right to mark verified numbers as spam or block them completely. E-commerce investor Upper90 raises $55M for equity investments. Upper90 is led by CEO Billy Libby, former head of quantitative education sales at Goldman Sachs, and Chairman Jason Finger co-founder of Seamless, and it was the first investor in both Thrasio and Clearbanc. The firm offers debt and equity funding, and it just closed a $195 million fund in December. Chili Piper, a sophisticated SaaS appointment scheduling platform for sales teams, raises a $33 million B round led by Tiger Global. Existing investors Base10 Partners and Gradient Ventures, Google’s AI-focused VC, also participated. This brings the company’s total financing to $54 million. The company will use the capital raised to accelerate product development. The previous $18 million A round was led by Base10 and Google’s Gradient Ventures nine months ago. Substack announces a $1M initiative to fund local journalists. The startup described Substack Local as a $1 million initiative that will fund independent writers creating local news publications. Similar to the Substack Pro program, the company will offer cash advances of up to $100,000, as well as mentorship and subsidized access to health insurance and design services. In exchange, Substack will take 85% of subscription revenue for a year.UserZoom raises $100M and acquires EnjoyHQ, to grow its platform to improve UX and other interactive design elements. It has built a platform used by companies like Google, Microsoft, PayPal, Salesforce, and many others to help them stay off the bad design radar with tools to evaluate their design and identify where and when it doesn’t work.MedChron LLC Launches Its Innovative New SaaS for Small to Mid Size Medical Practices, Optimizing CCM, CCP, and MWV Medicare Billing. MedChron was founded to fix problems and deliver an affordable web-based software solution that quickly, efficiently, and neatly organizes all contacts and interactions with patients. 

What is Augment?

Augment by Center for Global Innovation and Leadership Development is a podcast exploring how organizations, leaders, and cultures are evolving in the age of AI. Each week, we dive deep into the human side of technological transformation, examining how the most successful organizations are reshaping leadership, culture, and organizational design for an AI-driven future.

This isn't just about implementing AI tools. It's about fundamentally rethinking how we lead, build culture, and create organizations that thrive alongside artificial intelligence.

Through candid conversations with CEOs, organizational leaders, and culture architects, we explore the critical questions:

How do leaders adapt their approach when AI changes everything?
What does organizational culture look like when humans and AI collaborate?
How do we build resilient, adaptive organizations for an uncertain future?

What we feature:

Leadership strategies for navigating AI transformation
Cultural shifts required for human-AI collaboration
Organizational redesign for the AI era
Case studies of companies successfully evolving their culture
Frameworks for building AI-ready leadership capabilities
The psychology of change in technology-driven organizations

Augment is your strategic guide to leading organizations and shaping culture in the age of AI — where human wisdom and artificial intelligence create unprecedented possibilities.

Subscribe and join the conversation about the future of organizational leadership.