Leslie Greenwood

Chief Evangelist, Community Strategist, Co-Founder of Wednesday Women, Startup Advisor, Ex-Stay-At-Home Mom

I'm the Co-Founder of Wednesday Women and the Founder of Chief Evangelist Consulting: two ventures grounded in a core belief: community isn’t a tactic, it’s a force.

Wednesday Women began as a ripple in 2023 as a small, intentional effort to elevate executive women. We amplify women’s voices on LinkedIn, on stages, on podcasts, not as polished personas, but as their real, remarkable selves (the woman behind the title). Our public platform is for everyone, and we’ve built a private membership for executive women who want to go deeper with that mission and create connections both help unlock challenges but also are their biggest cheerleaders. 

Through Chief Evangelist Consulting, I help companies design community strategies that create lasting engagement. With 20+ years in customer-facing leadership roles, I approach community as a strategic lever, rooted in trust, value, and connection.

At the heart of everything I do is a belief in the power of evangelism, authenticity, and shared momentum.

And yes — I run on coffee, dark chocolate, trying (and failing) to keep me very vocal dog in check and talking loudly about diversity in tech.

Ambassador

Advocating for Pavilion’s mission of helping every leader and their team achieve their professional potential through community-powered learning. I will be supporting key initiatives, developing and teaching curriculum for Pavilion University and providing over 10,000 members with leadership advice. Join us at joinpavilion.com.

Dustin Joost

Osano

Osano, a leading data privacy platform, simplifies privacy compliance by helping organizations build, manage, and scale their privacy program to increase trust, stay compliant, and do the right thing.

Chief Revenue Officer (CRO)

Various Companies

On the side, I channel my passion for building companies and communities into investing and advising great organizations, funds, and leaders. A few that I've been involved with:

► GTMfund - the BEST early-stage VC focused on B2B SaaS startups comprised entirely of operators and builders (GTMramp Member)
► University of North Texas College of Business Board of Advisors Member - shaping the curriculum for future business leaders (Advisor)
► Aragorn.ai - the simplest integration platform as a service for IT and People Ops (Advisor)
► Mutiny - AI-powered 1:1 microsites and account intelligence for B2B companies (Investor)
► Gorgias - customer service platform specifically designed for e-commerce businesses (Investor)
► Spekit - just-in-time enablement platform, purpose-built to transform how sales reps operate (Investor)
► Hatchet Ventures - helping underestimated founders build scalable, successful companies (Advisor)
► Gartner Peer Network - helping CROs and CMOs navigate ever-changing market dynamics (Ambassador)
► Vasco - Science-based revenue platform for businesses building predictable revenue (Advisor)
► Offsight - manufacturing project management software for the offsite construction & building products industry (Investor)
► TrustPage - turning security assessments into revenue accelerator (Investor)
► Givz - e-commerce marketing platform turning discounts into donations (Advisor)
► Hunova - AI-powered talent assessment platform (Advisor)

Investor & Advisor

Pavilion

Pavilion (formerly Revenue Collective) is a support network for revenue leaders. We mentor each other, nerd out on GTM strategies and tech stacks, and collectively help each other build great organizations. 

I'm a guest lecturer in Pavilion's CRO and Forecasting schools where I teach about annual planning, funnel conversion models, sales and marketing alignment, and cohort modeling from seed stage to IPO.

DFW Chapter Co-Founder | CRO School and Forecasting School Guest Lecturer

Trivie

Built out a hybrid product-led growth and product-led sales go-to-market organization in the learning and development space.

Executive Vice President, Growth [Acquired by Quantum5]

Blackbaud

After Blackbaud's acquisition of YourCause in January of 2019, I led the integration and continued growth of our sales and marketing organization, including go-to-market efforts in Canada and the U.K., and served as an executive leader overseeing the broader integration of YourCause into Blackbaud.

VP, Sales - YourCause | Corporate Solutions [Post-Acquisition]

YourCause

I was an early employee and executive team member who helped build YourCause from <$1M ARR to over $40M, getting acquired in January 2019 by Blackbaud. During my time we grew from <10 employees to nearly 200, <1M users to nearly 10M across more than 500 Fortune 1000 companies in 170+ countries. From inception to acquisition we processed over $5B to charities and tracked more than 45M volunteer hours. 

I was fortunate to build YourCause's enterprise sales, marketing, and business development teams from the ground up, starting with just two sales executives, a marketer, and less than $1M in revenue. I developed and led the full stack sales and marketing team comprised of sales executives, business/sales development representatives, sales operations, market development, product marketing, RFP and proposal management, sales enablement, channel partnerships, and a few all-star marketers. As an executive team member, I helped lead the company through Series A and Series B funding rounds, 1 complimentary and 2 competitive acquisitions, and our own acquisition by Blackbaud after maintaining 60% client growth every year since 2012 and a 99% client retention rate. We were proud to be named one Dallas’ Top 100 Best Places to Work, Tech Titan’s Fastest Growing Companies, and an Inc. 5000 company multiple years in a row.

Simply put, YourCause is a technology company that connects corporations and their employees to the causes they care about. Our SaaS-based CSRconnect Platform is a fully hosted and managed solution used to engage employees in volunteering, giving, and diversity and inclusion initiatives, as well as help grant administrators manage their corporate and foundation philanthropic programs.

VP, Sales and GTM [Acquired by Blackbaud, Inc. NASDAQ:BLKB]

Promoted to VP of Sales and Marketing in December 2016.

Director of Sales and Marketing

Promoted to Director, Sales and Marketing in December 2014.

Sr. Sales Manager

Sales Manager

Sales Hacker, Inc.

Sales Hacker DFW was established to build a community of people, ideas, and organizations that are creating the next generation of sales and marketing teams. We are a community organization that provides educational and insightful events, content, and opportunities for collaboration centered around building predictable revenue. After growing the community to more than 800 members and becoming an official hub of Sales Hacker, Inc., we transitioned ownership and management of the organization to the Enterprise Sales Forum.

Co-Founder, Sales Hacker DFW

Digital Dallas

Digital Dallas is a community organization that helps to highlight all of the amazing things that Dallas is creating - from experiential marketing and robotics to interactive art and panels featuring leaders from a broad range of digital ventures. You'll find a little bit of everything at Digital Dallas events - programmers, marketers, artists, investors, entrepreneurs, and creatives. We come together to celebrate our love for technology, creativity, and innovation, all while learning from each other and having a little fun. Over the past 6 years, we've put on 50+ events and built a community of nearly 5,000 digital professionals and technophiles in the DFW area. Learn more at DigitalDallas.org. 

Before serving as the VP of Sponsorship I served as the VP of Membership, Co-VP of Marketing, and Director of Corporate Outreach.

Board Member, VP of Sponsorship

Insight Global

Insight Global is ranked as the 9th Largest IT Staffing Firm and 5th Fastest Growing. The company specializes in long and short term contract and contract-to-hire engagements. During my time at Insight Global I managed a portfolio of 40 accounts, developed MSA partnerships with 8 national accounts and over 50 different divisions spanning 25 Fortune 500 companies, resulting in approximately $780,000 in short-term revenue. I also built a team of 7 direct reports ranging from recruiters to account managers.

Account Executive

Pi Kappa Alpha

Represented a 240,000-Member International Organization with extensive sales travel to more than 36 accounts in 18 states and Alberta, Canada evaluating the strengths and weaknesses of the organization’s finances, recruitment (sales), marketing, real estate, and risk management programs.

Management Consultant

I build high-growth revenue organizations with a focus on sales and marketing alignment, story-based sales, and GTM motions that meet customers where they're at. I do this by creating environments where people are empowered to pursue their intellectual curiosity - authentically understanding our customers and each other so we can solve problems. 

With two exits and experience building in VC-backed (seed, series A, series B), Growth Equity (series B), and publicly traded companies ($4B+), I'm a dynamic executive that knows how to put together teams that help companies scale. 

GTM strategies I've developed and deployed: 
- Enterprise sales ($100K - $1.5M ACVs) 
- Product led growth (PLG)
- Product led sales
- High velocity, high volume ($5k - $50k ACVs; SMB and MM) 
- Inorganic growth/mergers and acquisitions (both as the acquirer and acquired)
- Multi-product platform (land and expand + platform upfront) and point solution

Industries I've served: 
- B2B and enterprise Software-as-a-Service ('SaaS'​)
- Software-Plus-Service ('SPS'​) technologies
- Data privacy
- Governance, risk, and compliance ("GRC")
- Third party risk management ("TPRM")
- Cybersecurity
- Fintech (payment processing)
- ecommerce
- Legaltech
- HR and employee engagement technologies
- AI/ML-based SaaS
- Business intelligence and analytics
- Learning and development
- Managed IT services (ERP, Cloud, Managed/Professional Services, Infrastructure, and Programming) 
- Social and corporate impact

I also advise startups and consulting groups on topics related to go-to-market strategy, sales and marketing alignment, and annual planning + execution. 

What it comes down to is that I enjoy and excel at building and leading strong groups of passionate individuals to do really cool things. All with the hope to do a little good. I'm active in the technology, nonprofit, startup, and educational spaces through my work with Social Venture Partners Dallas, Pavilion (formerly Revenue Collective), The Dallas Heroes Project, and the University of North Texas College of Business.

Let's be honest though - my two kids, wife, and golden retriever are way cooler than any of the above.

taplio

The Battle

Leslie Greenwood

Dustin Joost

Followers

Posts

Engagements

Likes

Ready to grow your LinkedIn presence?