Gradual

GTM Strategy, Advisor to CEO

“Jill’s unmatched expertise in sales, community building, partnerships, and ecosystems has been pivotal in shaping our product vision and go-to-market strategy. Her unique insights and strategic connections have unlocked new opportunities and accelerated our growth.” – Jerry Li, CEO & Founder

Gradual is a community platform that centralizes all community experiences, driving product adoption and deeper customer relationships.

Strategic Advisor

Stage 2 Capital

Stage 2 Capital invests in early-stage B2B software companies and sits shoulder-to-shoulder with leadership teams to operationalize sustainable revenue growth. We provide expertise and capital to help companies scale. 

Our LP base of 500+ seasoned GTM executives is matched with the strategic and operational needs of our portfolio companies. We involve our network in 100% of our investments, which often includes joining a portfolio company as an executive, board member, or advisor.

In 2018, I helped raise our $15 million Fund I from LPs at Asana, Atlassian, Box, Gong, HubSpot, Okta, Slack, Salesforce, SAP, ServiceNow, Toast, Twilio, Workday, Snowflake, Zoom, and many others.

$15m Fund I, LP, and Associate Member
$80m Fund II, LP
$150m Fund III, LP

GTM Advisor & LP

Klue

GTM Advisor

Competitive Enablement platform that combines market, competitor, and buyer insights.

Raised $81 million from top VCs including Salesforce Ventures, Tiger Global, Craft, and OMERS Ventures.

Advisor

Folloze

Advisor to the CEO

Enterprise customers include Adobe, Autodesk, DocuSign, Okta, VMware, UiPath, Cisco, and ServiceNow. 

Integration partners feature 6Sense, Demandbase, Marketo, Outreach, Qualified, and Salesforce.

nearbound.com

Assisted in the design, launch, and growth of the Nearbound category at Reveal. In June 2024, Reveal merged with Crossbeam, with the unified focus now on driving Ecosystem-Led Growth.

While outbound interrupts and inbound attracts, nearbound surrounds.

Nearbound is essential because buyer behavior has shifted from the ‘How’ economy to the ‘Who’ economy. Buyers now ask, ‘Who can help me solve X?’ and seek out trusted nodes in their network.

Strategy & Champion

Guild

Advisor to the B2B GTM team.

On a mission to unlock opportunity for America’s workforce. When opportunity is as evenly distributed as talent, everyone benefits. Individuals rise, companies grow, and our economy thrives.

In June 2022, Guild raised a $175 million Series F funding round at a $4.4 billion valuation. The round was led by prominent investors including Bessemer Venture Partners, Cowboy Ventures, Emerson Collective, General Catalyst, GSV, ICONIQ, Redpoint, Workday Ventures, Salesforce Ventures, and Oprah Winfrey.

GTM Advisor

LoopVOC

Voice of the Customer software for B2B SaaS Companies. Advisor to CEO & Founder.

Affinio

Member Board of Directors

Sales for Life

Advisor & Partner

Nudge.ai

Acquired by Affinity, a relationship intelligence platform.

Advisory Board Member & Investor

23 years in B2B SaaS Go-To-Market at Salesforce, Eloqua, HubSpot, Marketo. Customer Obsessed. Partner Obsessed. Living-In-Market. LinkedIn Member #320,966

Majored in Customer. Minored in Go-To-Market. Live in-Market. 

24 years in B2B SaaS. Early employee at Salesforce (first 100), Eloqua (#13), HubSpot Advisor (2014-2016), Marketo (2018).

Love startups, especially category creators.

Born Sales. Bred Marketing. Building Partnerships. 

I spent six years in management consulting, 52 quarters in software sales at Salesforce and Eloqua, six years doing professional speaking, 2018 reporting to the CEO of Marketo (acquired by Adobe for $4.75B), Limited Partner "LP" and GTM Advisor at Stage 2 Capital and GTM Fund. 

I started investing in 2012 and maintain my personal portfolio of investments in sales and marketing technology startups. I also started advising startups in 2012 and joined my first Board of Directors in 2016. Four of the companies I've advised have had successful exits -- HubSpot, Accompany, DataRPM, and PartnerHacker. 

My work keeps me focused on the changing B2B buying environment and what revenue teams need to do to evolve their culture, skills, processes, data, and technology. 

****If you want to connect with me on LinkedIn, don't send a generic invite.****

Jill Rowley

guHRoo payroll & hr

I worked for a large corporation when I moved to South Carolina in 2010. I called up to “corporate” one day to ask for a few hundred dollars to sponsor an event for a local non-profit.

“Matt, we just don’t get involved at the local level.”

I remember this conversation as clear as day. My family and I were putting down roots in South Carolina and wanted to be a part of the community. For us, this meant supporting the causes we care about and being a part of a company that cared about our community. 

When I couldn’t find a company in my industry that aligned with these goals, we created our own. 

We give away 5 percent of our company to local charities. That includes three percent of all revenue, one percent of our product, and one percent of our time volunteering (come serve with us!).

Interested in how we solve human resources problems for small businesses? Grab a time on my calendar here: https://meetings.hubspot.com/matt702/15-minute-intro-call

Outsourced Scale

We provide small businesses with virtual, offshore teammates, powered by AI.

Partner

Underdog Digital

We grew frustrated with how digital marketing agencies treated us and their ability to produce results. We built our own process, 10xed our leads, and started replicating the process for others. Small business marketing simplified.

GrowCo Columbia

Founder, President of the Board of Directors

Some tech company 

Sr. Sales Executive

The big red machine 

District Manager

I was so proud when my company finally grew enough to offer health insurance to my team. I thought I was being a great employer.

Then one of my employees told me bluntly: "It would be more expensive and worse coverage for me to use our plans."

That stung. But what really opened my eyes was talking to one of our clients who was trying to recruit against companies like Facebook. They were showing potential hires age-banded plans and getting beat every single time.

I realized this wasn't just my problem - small businesses across South Carolina were losing the talent war because of benefits.

I knew you couldn't have a PEO in South Carolina without Blue Cross. In our state, they're the only carrier that matters. So I didn't just find a solution, I built one.

It wasn't easy. Blue Cross has strict size requirements and won't work with just any agent. But I was determined to give small businesses the same buying power as Fortune 500 companies.

Today, we've helped hundreds of South Carolina businesses compete for top talent, saving an average of $50K annually. 

Our biggest win? 

A 21-employee nonprofit that we saved $120K per year - money they used to hire a new teammate to grow their mission instead of padding insurance company profits.

If you're tired of losing talent because your benefits can't compete with big corporations, or you're spending too much on insurance that your employees don't even value, let's talk.

Every dollar you save on benefits is a dollar you can invest back into growing your business and taking care of your team the way they deserve.

Book a time with me here: https://go.guhroo.co/ty-page-2921-8170

taplio

The Battle

Jill Rowley

☞ Matt Vaadi

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