Chief Operating Officer, Optimism Global

New York, NY
Pardon Ventures – Optimism /
Full Time /

Optimism is a media company working to build a brighter web. We conceive, launch, and operate high-quality digital brands that spark curiosity, spread positivity, and improve the lives of our readers. With an inbox-first approach, our hope is to transform email into a healthy alternative to social media feeds, a place where you can curate the news, entertainment, and information you truly want and enjoy.

Our brands populate a variety of lifestyle categories: including travel, learning, home, health & wellness, finance and more. Our universal approach helps us reach 15 million subscribers across our network and serve more than 30 million web sessions each month. And we’re growing with each new brand and newsletter launched.

Optimism Global is a roll-up of original ventures and their brands including: The Discoverer, Inbox Games, Likemind, and early stage concepts including Nice News; as Chief Operating Officer (COO) you will play an active role in further uniting the company and creating a thriving culture across the business units and an active venture studio model.


We are hiring this role to create more unified management, to help elevate our founder out of the day-to-day, and to evolve the company further into a performance-driven content organization with a data-informed mindset (e.g. tracking metrics that matter and executive and organizational dashboards that bring full clarity to all members of the team on business performance) – ensuring all teams are using high quality data to make decisions, drive growth, and produce revenue. 
As we move into a new age of digital media, it is paramount that the company leverage its valuable email audiences and rich brand portfolio to continue to build reader trust while it transcends dependency on programmatic and cookie-supported advertising, and develop strong performance driven and brand direct revenue channels.

As the COO, you will be accountable for…

Strategic Integration

    • Learn from Optimism’s founder, Nicholas Pardon, what insights and tactics have enabled Optimism to scale high quality content in the inbox.
    • Come to act as the “email proxy” for Nicholas in Optimism management conversations and product reviews, so that he can effectively spend less time “in” the business and more time “on” the business, resourcing it and developing more advanced growth projects.
    • Come to act as a key business partner and strategist across the Pardon Family Office holdings in digital publishing, helping coordinate and choreograph which ventures are funded and launch, and how ventures make use of shared resources and data to effectively become more than the sum of their parts.
    • Collaborate and build with Pardon’s Venture Partners, leads for other smaller business units across the operating portfolio.
    • Ability to take a vision and develop an executable metrics based plan.

Managing Key Functions: Directly manage functional leads of the core pillars of the business, driving high performance in each and effective cross-org collaboration

    • Brand. This function includes brand origination and design, visual and voice design, and the entire set of workflows and teams that generate the content for our brand portfolio.
    • Email. This function includes our email sending infrastructure, campaign design and execution workflows, audience segmentation, and is closely related to brand “cross-pollination” growth strategies.
    • Growth. This function (which does not currently have a dedicated leader) includes user/audience acquisition and growth marketing for our brands.
    • Revenue. This function does not currently have an executive lead; you will play “Interim Chief Revenue Officer” as COO until that role is scoped and required for the business. This function looks holistically at the revenue channels (programmatic, performance, brand sales) to help allocate resources and make decisions to a)grow revenue and b) diversify correctly across these channels, as historically programmatic has been overrepresented in our revenue mix.
    • Programmatic. We have a small in-house programmatic ads team.
    • Sales. We have a sales leader and a small account management team.
    • Performance. We have a newly hired performance/affiliate lead.
    • Platform. This function includes product design and development, engineering, and data infrastructure.
    • People & Culture. Over time, develop a People function (which is currently resourced directly from the Pardon Family Office).

Business Results

    • Cultivate and drive a thriving and engaged culture across the entire company and portfolio.
    • Put the Optimism business on an effective management cadence with comprehensive  reporting to drive business results while maintaining a high standard for quality of work.
    • Hold function leaders accountable for hitting their goals, and work with leads to resolve any differing views or impasses.
    • Implement an effective system of quarterly goals for all functional areas of Optimism Media and hold accountability on the achievement of these metrics to the Pardon executive team.
    • Open an Optimism office in Southern California, and institute a hybrid of IRL work culture.


    • Have considerable experience working “in the inbox” ideally with a combination of email content/newsletters, email marketing, email products, and email technology/tools.
    • Have a strong familiarity with the wider world of digital media and publishing, are aware of key trends and challenges, and have conviction that strong email DNA is a source of competitive advantage for the next decade.
    • Are highly entrepreneurial, with heavy experience managing teams and businesses. You know how to lead executive teams and you are at the point in your career where you want to invest the time and attention to warrant significant upside in the business(es) that you incubate and lead.
    • Have an appreciation for arts, culture, and lifestyle, as these themes are key elements of the Pardon Family Office, which owns all Optimism holdings.
    • Have a strong appreciation for performance and historical track record of driving organizations to hit performance-based metrics.
This role will be considered a Venture Partner of the Pardon Family Office; in addition to executive compensation package (base salary, bonus, equity), the role will have perks and benefits associated with the Family Office.


Pardon Ventures is the operating company for the Pardon Family Office and oversees a portfolio of digital media companies that transform how people see the world. As a team of creative entrepreneurs, we develop and launch digital ventures that foster community, encourage new ways of thinking, and create the context for positive change to occur. Our original ventures include an inbox-first travel magazine, a positive news publication, and a collection of media brands that spark wonder and curiosity, all of which are enjoyed by millions of readers every day.

This role will be based in Orange County, Los Angeles or New York. The Family Office is open to covering  relocation for the right fit.

Our Commitment

We aim to provide equal opportunity for all. We are firm believers in the strength of diversity and aim to build teams of individuals that offer unique perspectives, come from different backgrounds, and challenge each other to be better every day!