Co-Founder & Chief Revenue Officer at Sales Assembly | Developing the GTM Teams of B2B Tech Companies | Investor | Sales Mentor | Decent Husband, Better Father

I’ve spent my career trying to solve one puzzle: how do you scale sales teams without losing what makes them great?

Before Sales Assembly, I lived the highs and lows of hyper-growth - leading revenue teams, juggling targets, and realizing that growth without structure eventually collapses under its own weight. The lesson stuck: great teams don’t just grow fast, they grow well.

That’s the idea behind Sales Assembly. We built the preeminent skill development platform for B2B tech companies: part training, part community, part therapy for GTM leaders trying to do more with less. We help teams move faster, stay aligned, and actually enjoy the process of getting better.

Somewhere along the way, I also became a General Partner at VentureOn Partners, Chapter Head at Pavilion, and mentor with Techstars. I’ve spent a lot of time with founders and operators who are chasing the same thing: building something that lasts without taking themselves too seriously.

A client and friend once described me as someone who “builds community through authenticity,” which I’ll take as the polite version of “tells it like it is.” That’s probably fair.

Outside of all that, I’m a decent husband, a better dad, and a walking Simpsons encyclopedia (seasons 1–11 only, of course). I travel when I can, laugh often, and still believe a good team - and a good joke - can get you through just about anything.

Matt Green

Spoke with a guy launching a company in stealth. His entire outbound strategy has been hundreds of handwritten notes. 6 months in, they're deploying ten Fortune 500 clients.

Not emails. Not LinkedIn messages. Not AI-powered video prospecting.

Actual handwritten notes. With a QR code to book time. Mailed to every executive he'd ever worked with.


Sounds bonkers, but actually makes perfect sense. I mean, I get that it's 2025. Sure, we have AI that writes perfect emails. Sequences that personalize at scale. Prospecting tools that know what cereal your buyer ate for breakfast.

But the gangster move is a stamp.


He told me what happened at dinner that kicked off his whole strategy.

He's breaking bread with an old contact. CRO of a $12B company. 3,000 employees. The exact buyer every SaaS vendor is chasing.

My guy mentions he's been emailing him. Ten times over a few months. Zero response.

The CRO laughs. "Oh, I don't read my inbox anymore. Just email my chief of staff if you want to get a hold of me."

Not "Sorry man I'm swamped." Not "Shit I think it went to spam."

He literally doesn't open his inbox. Ever.


Here's what's wild about this moment we're in:

We've spent three years building AI that writes better emails, crafts better subject lines, personalizes at scale. Meanwhile, the entire ENT buying committee has collectively decided to ignore ALL of it.


Every inbox will be perfect in 12 months. Every email will look hand-crafted. Every message will reference that podcast you were on or that article you wrote.

Which means every email will still be just noise. It'll be "better" by today's standards, but noise nonetheless.


But a handwritten note? That's a human being who gave a shit for 90 seconds.

That CRO gets 847 emails a day. 840 of them are vendors who "noticed he recently raised a Series C" or "thought his CEO's comments on the last earnings call were really compelling."


AI didn't kill email outbound. AI made it so good that everyone's doing it. 

Which is what killed it.


There's a huge shift right now going back towards relationship selling. It would be a bit romantic to think it's because it's noble or pure.

But in reality, we're going back to it because AI made everything else worthless.


Handwritten notes. Showing up at the conference. Actually knowing someone before you try to sell them something.

Sure, old farts like me might think it's romantic. But at the same time, you can also just consider it math.


When everyone can send a perfect email, nobody's reading email.

And yeah, the kinda stuff this guy did is harder. That's why it works.

CRO of Sales Assembly | Decent Husband, Better Father

OneScreen.ai

First marketing leader hired to help midmarket marketers add measurable outdoor advertising to their media mix.

I am delivering 90% of sales pipeline as a team of one through demand generation, inbound marketing, field marketing, product marketing and sales enablement.

Head of Marketing

Cohosting a new podcast from OneScreen.ai where we interview marketing experts about brand marketing, how they use out-of-home advertising in their marketing mix and much more.

Co-Host and Executive Producer Beyond the Billboard Podcast

GTMfund

GTMFund Member

Send

First US-based hire to grow the most advanced digital underwriting workbench for insurance carriers, MGAs and specialty insurers.

I oversee growth for the US market including business development and partnerships along with demand gen and GTM globally. 

Built a BDR sales function and team from scratch.

Leading demand generation, SEO, PR, email marketing, field marketing, event marketing, RevOps and more for a global insurtech startup selling enterprise SaaS to global and regional insurance companies.

VP of Marketing

Charlieriley.com

Fractional head of marketing consultation for regional and national brands and government, along with home, real estate and advertising and marketing agencies. 

I helped companies looking to hire their first marketing leader or who cannot bring on a full-time marketing leader with branding, growth marketing, product marketing, demand generation, sponorships, partnership marketing, sales alignment, event planning, media, and public relations advice for improved sales, greater consistency and enhanced awareness.

I have worked within SaaS, cybersecurity, manufacturing, digital signage, B2B, self storage, education, hospitality, healthcare, athletics, non-profit and other industries on marketing planning such as designing and implementing social media campaigns, market research, copywriting, media buying and more.

Chief Strategy Officer

Havoc Shield

Executive hired to develop a US growth plan for this SaaS cybersecurity subscription startup leading sales, demand generation, product marketing, brand marketing, partnerships, growth and partnerships.

-Doubled customer count through demand generation, ABM customer acquisition and marketing automation (HubSpot) best practice integrations
-Helped build a new product focused on insurance brokers and their insureds to help meet cybersecurity questionnaire standards. Built and executed Go-To-Market plan to validate product and sell to learning US insurance brokers
-Built a partnerships and channel sales program, having negotiated and landed an exclusive reseller program acceptance with one of largest global SaaS distributors
-Helped launch a cybersecurity insurance reselling product based on customer and prospect research focused on the insurance brokers and wholesaler networks
-Mentored an SDR team to implement consistent sales motions, ABM tactics, outbound sales sequences and aligned marketing with sales enablement efforts
-Created the only national, exclusive Chambers of Commerce referral program through a nurtured business development strategy
-Landed 30+ podcast, published media and conference speaking slots and appearances along with rebrand
-Executed an Appsumo deal

Havoc Shield is cybersecurity startup that delivers an all-in-one suite of proactive cybersecurity tools like vulnerability scans, penetration testing, phishing training, security questionnaires and other tools to satisfy compliance requirement for small businesses and startups to win new deals and protect themselves from ransomware and cybersecurity attacks.

VP of Growth

Pharmacy Benefit Dimensions

First head of marketing and revenue leader hired in a brand new role to create a cohesive sales and marketing team to drive demand generation, retention marketing efforts, implement data-driven decision making and growth marketing efforts for this national healthcare pharmacy benefit manager selling to SMB and Enterprise insurance brokers, healthcare plans and more.

Senior leadership team member hired 2 weeks before the COVID 19 pandemic, leading the communications and work-from-home transition efforts of over 100 employees to transition to a remote environment. 

-Led team of 8 marketers and salespeople for this $26MM national pharmacy benefit manager. 
-Exceeded revenue budget by 28% in 2020
-Oversaw the RFP process and team, implementing a centralized RFP tool for faster and more accurate RFP responses
-Implemented HubSpot for CRM and marketing automation, created a new inbound marketing and lead generation strategy while improving web traffic activity 19% year-over-year
-Developed an internal communications process to alleviate concerns and keep associates informed and entertained on important information daily during a remote work transition

Director of Sales and Marketing

Curbell Plastics

Recruited to the senior management team to lead a team of 8 in business development, sales support, marketing and communications for a $190 million industrial plastics distributor. Had P&L and KPI responsibility, customer acquisition lead, manufacturer supplier partnerships management, and oversight of PR and ad agencies. Managed M&A communications along with sales, marketing, and business development alignment. Collaborate on sales itinerary planning, prospecting, and communications training.
-50 percent B2B e-commerce revenue improvement through site optimization, content marketing and inbound marketing (Hubspot) implementation
-35 percent B2B qualified lead generation increase
-17 percent organic traffic growth year-over-year 
-UX best practices implementation reduced cart abandonment 5 percent
-Built a product marketing feedback loop, including launching Net Promoter Score (NPS) for real-time customer feedback, improved retention and customer marketing content creation

Director of Marketing

Lawley

First-ever head of marketing leader hired onto the leadership team managing a team of 4 who oversaw all growth marketing, product marketing, advertising, public relations, social media, SEO, SEM, research and communications and Revenue Ops for this Top 50 independent insurance broker.

-Helped agency eclipse record sales growth each year of my tenure
-Launched new, SEO-optimized website delivering 182 percent organic traffic growth and a 22 percent Alexa ranking improvement year-over-year with 400+ published sales and educational content pieces
-Launched an Account Based Marketing (ABM) strategy focused on targeted landing pages, presentation materials and custom content for key mid market and enterprise accounts
-Implemented marketing automation (Pardot/SalesForce Marketing Cloud) into CRM (SalesForce)
$370,000 plus in estimated media value earned through social media employee advocacy marketing program built for customer service, employee recruitment, and lead generation
-150 percent improvement in social media reach
-100+ events executed including webinars, seminars, focus groups, and sponsorships
-Landed dozens of PR interviews and guest posts through thought leadership and internal media training
-Executed company-wide rebrand to deliver consistent messaging to cross-sell over 80 product lines
-Built vendor and partner co-op marketing program
-Developed and nurtured company-wide intranet and communications platform for all associates
-Worked with dozens of nonprofits on sponsorship allocation, activation, and fulfillment
-Communications and PR efforts led Lawley to be named as 2015 Company of the Year by Buffalo Business First
-Co-managed the sales operations team, supporting over 100 salespeople, data integration and sales software

Director of Marketing and Communications

PLS 3rd Learning

Recruited for inaugural executive team position overseeing marketing, business development, and customer engagement strategy and development for this international education technology startup.
-Helped land an RFP valued at over $4 million, the largest win in company history, through an Account Based Marketing (ABM) campaign with custom videos, testimonials, presentation collateral all housed on a unique URL landing page
-Managed marketing budget of over $1 million, outside agency vendors and team of 7 across multiple offices
-Product marketing lead for various digital and international projects creating the first customer advocacy panel, conducting consistent qualitative and quantitative customer research checkins and more
-Rebranded 2 companies into 1 cohesive brand, melding B2B and B2C SaaS and traditional learning models
-Took over public relations and internal communications while helping merge 2 companies in 1
-Marketing and development efforts secured a multi-year, multi-million dollar state contract and increased lead generation for multiple larger-scale education projects
-Implemented project management (Basecamp), CRM (Highrise), email and landing page A/B tests, focus group research, and managed national and international trade shows and events 
-Built thought leadership and employee advocacy outreach securing multiple conference and media speaking opportunities

Chief Marketing Officer (CMO)

FARM Buffalo

Oversaw all digital projects for this full-service advertising agency, ranging from digital media placement, email marketing campaigns, user experience (UX) and digital strategy, social media, QR codes, mobile marketing, Search Engine Optimization (SEO), Search Engine Marketing (SEM), landing page development, compilation and analysis of market research and web analytics and online direct marketing applications. Developed online and offline strategy for current and prospective clients in the grocery, automotive, CPG, retail, real estate and financial industries. 

I also managed public relations and served as social media/customer service community manager for the agency and several of our clients, along and internal and external communications.

Digital Marketing Director

Leading Marketing at OneScreen.ai | VP-level Revenue Generating Marketing Leader | 3x Dad | Podcast Host & Former CMO

I'm a transformational revenue-generating marketer, having owned a sales number as a former Chief Marketing Officer (CMO), blending brand marketing with demand generation, focused on delivering sales. 

I've been recognized as a Top 50 B2B Marketing Influencer to Follow, knowing how to build a sales-aligned marketing function from scratch or capable of upleveling a current marketing team in a variety of ways, leading global internal or growing through outsourcing with partners, agencies, and vendors. 

As a seasoned, experienced marketer, I specialize in standing up demand generation, account-based marketing (ABM), partner marketing and sales enablement, currently delivering 90% of the sales pipeline through inbound channels. My work redefines outdoor advertising with creative innovations that extend beyond traditional formats, empowering brands to elevate their marketing mix.  

I co-host and produce the Beyond the Billboard Podcast, where we engage marketing experts to explore brand strategies and OOH applications. By combining my branding expertise with a passion for growth, I help businesses unlock new opportunities in a competitive SaaS landscape, staying committed to collaboration and measurable outcomes.

I'm passionate about coaching my kids' sports teams, playing competitive soccer, philanthropy, and event planning, including previously co-chairing Buffalo's AAF ADDY Awards and setting up my own fundraiser, the Buffalo Scavenger Hunt, benefiting Camp Good Days that supports kids with cancer.

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