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

Generic GTM is dead → Go to my featured section for actionable GTM insights and elevate your marketing game 🔥| Co-Founder of TACK | Creating the category of People-first GTM 👥| 13+ Years in B2B Marketing 📈

I help B2B companies build go-to-market strategies that prioritize real connection because relationships, not just reach, drive growth.

After 14 years in B2B marketing, I’ve led field marketing, demand gen, community, and influencer programs. I know what works, what doesn’t, and what’s changed.

Too many companies still treat buyers like leads. That’s not how modern GTM works.

I’ve helped 35+ B2B brands shift from transactional tactics to connection-driven growth, building scalable strategies, launching communities, running 30+ webinars, and rolling out on-demand models that replaced bloated in-house teams.

Today, I work directly with brands, founders, and marketers to build go-to-market engines that scale—without the spam.

What I do:
→ Build integrated campaign strategies that drive pipeline
→ Coach creators and brands on influencer marketing
→ Design community-led and field programs that actually work
→ Speak on GTM, content, and creator-led growth
→ Act as a fractional marketing leader or advisor

📚 Author of B2B Influencer Marketing: Work With Creators to Generate Authentic and Effective Marketing (Kogan Page, 2025)

👋 Let’s work together: DM me or visit https://linktr.ee/NickBMarketing

Nick Bennett

I wasn't a brand marketer.

I was the "pipeline now" guy. The "just get meetings" guy. The "who cares about brand when we need revenue" guy.

Then I watched the same movie play out at company after company.

10 things I learned the hard way about brand in B2B:

1. 𝗘𝘃𝗲𝗿𝘆 𝗦𝗗𝗥 𝘀𝗲𝗻𝗱𝗶𝗻𝗴 𝟮𝟬𝟬 𝗲𝗺𝗮𝗶𝗹𝘀 𝗳𝗼𝗿 𝗼𝗻𝗲 𝗺𝗲𝗲𝘁𝗶𝗻𝗴? 𝗧𝗵𝗮𝘁'𝘀 𝘆𝗼𝘂𝗿 𝗯𝗿𝗮𝗻𝗱 𝘁𝗮𝘅. You're literally paying for invisibility. In time. In burnout. In missed quota.

2. "𝗙𝗶𝘅 𝗽𝗶𝗽𝗲𝗹𝗶𝗻𝗲 𝗳𝗶𝗿𝘀𝘁, 𝘁𝗵𝗲𝗻 𝘄𝗲'𝗹𝗹 𝗶𝗻𝘃𝗲𝘀𝘁 𝗶𝗻 𝗯𝗿𝗮𝗻𝗱." I've heard this from every CEO. It's like saying "let me drown first, then I'll learn to swim."

3. 𝗬𝗼𝘂𝗿 𝗰𝗼𝗺𝗽𝗲𝘁𝗶𝘁𝗼𝗿 𝘄𝗶𝘁𝗵 𝘁𝗵𝗲 𝘄𝗼𝗿𝘀𝗲 𝗽𝗿𝗼𝗱𝘂𝗰𝘁 𝗸𝗲𝗲𝗽𝘀 𝘄𝗶𝗻𝗻𝗶𝗻𝗴? They're not better. They're just... known. Familiarity beats features every damn time.

4. "𝗧𝗵𝗲𝘀𝗲 𝗹𝗲𝗮𝗱𝘀 𝗮𝗿𝗲 𝗴𝗮𝗿𝗯𝗮𝗴𝗲." No, they just have no idea who you are. There's a difference between a bad lead and a cold lead. Brand warms them up before sales even talks to them.

5. 𝗕𝗿𝗮𝗻𝗱 𝗰𝗼𝗺𝗽𝗼𝘂𝗻𝗱𝘀. That competitor who's been blogging for 3 years while you were "waiting for budget"? Yeah, good luck catching up now.

6. 𝗧𝗵𝗲 𝗺𝗼𝘀𝘁 𝗲𝘅𝗽𝗲𝗻𝘀𝗶𝘃𝗲 𝗺𝗶𝘀𝘁𝗮𝗸𝗲 𝗶𝘀𝗻'𝘁 𝗼𝘃𝗲𝗿𝘀𝗽𝗲𝗻𝗱𝗶𝗻𝗴 𝗼𝗻 𝗯𝗿𝗮𝗻𝗱. It's underspending. Ask me how I know. Actually don't. It still hurts.

7. 𝗪𝗲 𝘄𝗲𝗻𝘁 𝗳𝗿𝗼𝗺 𝟮𝟰 𝘁𝗼𝘂𝗰𝗵𝗲𝘀 𝘁𝗼 𝟲. Same close rate. Only difference? People had heard of us. That's 18 touches your SDRs don't have to make.

8. 𝗕𝗿𝗮𝗻𝗱 𝗿𝗲𝗱𝘂𝗰𝗲𝘀 𝗖𝗔𝗖 𝗺𝗼𝗿𝗲 𝘁𝗵𝗮𝗻 𝗮𝗻𝘆 𝗴𝗿𝗼𝘄𝘁𝗵 𝗵𝗮𝗰𝗸. But nobody wants to hear that in a board meeting when pipeline is down 40%.

9. 𝗘𝘃𝗲𝗿𝘆 𝗯𝗼𝗮𝗿𝗱: "𝗪𝗵𝘆 𝗶𝘀 𝗖𝗔𝗖 𝗴𝗼𝗶𝗻𝗴 𝘂𝗽?" Also every board: "Cut brand spending, we need pipeline now." Make it make sense.

10. 𝗕𝗿𝗮𝗻𝗱 𝗶𝘀𝗻'𝘁 𝗳𝗹𝘂𝗳𝗳𝘆 𝗕𝗦. It's the difference between cold calling 100 people and having 10 people call you.

If I could go back and slap 2010 me:

Start content on day one. Not after product-market fit. Not after Series A. Day. Freaking. One.

Put 30% into brand even when it hurts. ESPECIALLY when it hurts.

Stop measuring brand impact at 30 days. That's like planting seeds and digging them up next week to see if they grew.

Document everything. Share the ugly parts. Be known for something before you try to sell something.

The brutal truth?

While you're in another meeting debating whether brand is "worth it," your competitor just became the default choice in your prospect's mind.

And once they own that mental real estate?

Your 10% better features mean exactly nothing.

15+ Year B2B Marketing Leader Turned Founder | ABM, Field Marketing & Events, Influencer Marketing & More | DM Me to Learn More

After working with 35+ B2B brands in 3 years, here's what's actually going to matter in 2026.

Not predictions. Not hot takes. Just patterns I keep seeing with companies that are winning right now.

𝟭. 𝗙𝗼𝗰𝘂𝘀𝗲𝗱 𝗔𝗕𝗠 𝗳𝗶𝗻𝗮𝗹𝗹𝘆 𝘄𝗼𝗿𝗸𝘀.

Every company says they do ABM. Maybe 10% actually do it right.

The difference? They pick 25-50 accounts MAX. They know the actual humans involved. They create experiences, not campaigns.

One client went from 500 target accounts to 30. Pipeline went up 3x.

𝟮. 𝗣𝗮𝗿𝘁𝗻𝗲𝗿-𝗹𝗲𝗱 𝗲𝗮𝘁𝘀 𝗲𝘃𝗲𝗿𝘆𝘁𝗵𝗶𝗻𝗴.

The companies growing fastest? They're not doing it alone.

Customer co-marketing. Influencer partnerships. Integration partners running your events. One customer selling to another customer.

Solo marketing is dead. Everything is partnerships now.

𝟯. 𝗕𝗿𝗮𝗻𝗱 + 𝗗𝗲𝗺𝗮𝗻𝗱 𝗳𝗶𝗻𝗮𝗹𝗹𝘆 𝘄𝗼𝗿𝗸 𝘁𝗼𝗴𝗲𝘁𝗵𝗲𝗿.

Stop arguing about brand vs performance. You need both.

The winning formula I'm seeing: 30% brand, 70% demand. But that 30% makes the 70% work 10x better.

We went from 24 touches to 6 at one company. Just because people knew who they were.

𝟰. 𝗘𝘃𝗲𝗻𝘁𝘀 𝗴𝗲𝘁 𝘀𝗺𝗮𝗹𝗹𝗲𝗿 𝗮𝗻𝗱 𝗺𝗼𝗿𝗲 𝘀𝗽𝗲𝗰𝗶𝗳𝗶𝗰.

The 500-person conference still exists. But the ROI is in the 8-person dinner.

VIP experiences. Executive roundtables. Customer advisory boards. Micro-events in tier 2 cities.

Quality > Quantity. Every single time.

𝟱. 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿𝘀 𝗯𝗲𝗰𝗼𝗺𝗲 𝘆𝗼𝘂𝗿 𝗯𝗲𝘀𝘁 𝗺𝗮𝗿𝗸𝗲𝘁𝗲𝗿𝘀.

Not just case studies. Not just referrals.

Customers creating content. Running webinars. Speaking at your events. Closing deals for you.

The best GTM teams are turning customers into an extension of their team.

𝟲. 𝗠𝗮𝗿𝗧𝗲𝗰𝗵 𝗰𝗼𝗻𝘀𝗼𝗹𝗶𝗱𝗮𝘁𝗶𝗼𝗻 𝗶𝘀 𝗿𝗲𝗮𝗹.

Not because of AI. Because CFOs are done with 120+ tools.

The companies winning? They have maybe 15-20 core tools. Everything else is noise.

Pick platforms, not point solutions.

𝟳. 𝗣𝗲𝗼𝗽𝗹𝗲-𝗳𝗶𝗿𝘀𝘁 𝗶𝘀𝗻'𝘁 𝗮 𝘀𝘁𝗿𝗮𝘁𝗲𝗴𝘆. 𝗜𝘁'𝘀 𝘁𝗵𝗲 𝗼𝗻𝗹𝘆 𝘀𝘁𝗿𝗮𝘁𝗲𝗴𝘆.

Your buyers are people with actual problems, actual budgets, and actual bosses breathing down their necks.

Talk to them like humans. Solve real problems. Make their lives easier.

The companies that remember this are the ones still growing.

𝗧𝗵𝗲 𝗯𝗿𝘂𝘁𝗮𝗹 𝘁𝗿𝘂𝘁𝗵?

None of this is revolutionary. It's just hard to execute.

But after 15+ years in B2B, I can tell you:

The basics done well beat innovation done poorly. Every time.

Anything you disagree with on the list?

20 things nobody tells you about being a terrible leader:

1. Hired someone toxic because they were brilliant. Kept them 8 months. Two people quit. Should've fired them week 3.

2. Your team knows when you're lying. Told mine everything was fine two weeks before layoffs. Trust never came back.

3. We're a family is BS. Families don't fire you when revenue drops.

4. Made my team work all weekend on a deck the CEO looked at for 90 seconds. That's when I learned to push back.

5. Your best performer will ghost you if you ignore them. Lost my best marketer this way. Still think about it.

6. CC'ing someone's boss just tells everyone you can't have real conversations.

7. 30 minute 1:1s are useless. Nothing real happens until minute 45.

8. Gave an all hands where I talked for 50 minutes straight. Someone actually timed it.

9. Promoting your best IC to manager usually ends badly. Different skills entirely.

10. Used to rewrite everything my team wrote. They stopped trying. Just waited for me to do it.

11. Your open door policy is meaningless if you're in meetings all day.

12. Brutal honesty without empathy is just being a jerk.

13. Remote teams need MORE connection not less. Real conversations. Not virtual happy hours.

14. Every pointless meeting costs 2 hours. The meeting plus getting back into deep work.

15. We need to move fast usually means I didn't plan and now it's your emergency.

16. Taking credit for your team's wins feels good for one week. Then they start interviewing.

17. Your weakest performer shows everyone what you'll accept.

18. First time I said I don't know what do you think everything changed.

19. If you're not uncomfortable weekly you're avoiding conversations that matter.

20. That person you can't lose? Already interviewing. Because you assumed they'd stay instead of earning it.

The difference between terrible leaders and good ones?

Terrible leaders pretend they never screwed up.
Good leaders tell you exactly how.

I've been awful at this. Multiple times. With witnesses.

But every time I admitted it my next team trusted me more.

Not because I got better.
Because I was honest about being bad at it.

Your early career disasters aren't failures.
They're your real education.

The only failure is pretending you were good from day one.

Nobody was. Especially not that VP you think has it all figured out.

20 things I learned putting people first in field and event marketing:

1. Partner events convert 3x better than solo ones. When their customers see your customers in the room, trust transfers instantly.

2. VIP experiences beat volume plays. 8 executives at a private dinner drove more pipeline than 800 people at our user conference.

3. Webinar engagement dies after minute 23. Unless a customer is talking. Then they'll stay for an hour.

4. The pre-event is the real event. Send personalized video invites. Call each attendee. Half your pipeline comes from pre-event touchpoints.

5. Micro events in tier 2 cities outperform major markets. Nashville beats NYC. Austin beats SF. People actually show up.

6. Your customer advisory board is your best event list. They'll bring the right prospects. Give them invite codes and get out of the way.

7. Event ROI takes 6-9 months to measure. That Q4 deal came from your Q1 dinner. Stop checking pipeline after 30 days.

8. Workshop format beats presentation format. Make them do something. Passive listening creates zero pipeline.

9. Regional field marketers should own the P&L. They know their market. Stop making them beg HQ for budget approval.

10. Partner with customers, not just vendors. Customer co-hosts bring qualified prospects. Vendor co-hosts bring whoever.

11. The 30/70 rule never fails. 30% customers, 70% prospects. Perfect mix for social proof.

12. Breakout rooms are where deals happen. Main stage is theater. Small rooms are sales.

13. Member communities 10x event attendance. Build the community first. Events become the reward.

14. Personalization at scale actually works. Custom landing pages. Role-specific agendas. Generic events are dead.

15. First-party data beats third-party intent. Track who engages with your content. Stop buying lists of strangers.

16. Executive sponsors matter only if they stay. Flying in for the keynote doesn't count. Dinner conversations close deals.

17. Follow up in 48 hours or don't bother. Day 1-2: 72% response rate. Day 14: You're forgotten.

18. Virtual events need 3x the production value. Bad audio killed more pipeline than bad content ever did.

19. Customer stories beat product demos. They care about people like them solving problems like theirs.

20. Word-of-mouth drives 60% of quality registrations. Focus on experience, not just attendance.

Spent a decade learning that events aren't about gathering people.

They're about connecting the right people.

The companies winning at event-led growth don't chase attendance metrics. They obsess over the quality of connections made.

But try explaining that when leadership wants to see "cost per lead."

Make your GTM more people-first and that means designing for relationships, not registrations.

Most companies are still shipping branded stress balls to convention centers wondering why nobody remembers them.

Nobody talks about the hardest part of internal marketing.

Getting your own team to actually give a shit.

I've watched brilliant campaigns die because sales didn't get it. Product roadmaps derail because engineering thought marketing was just making things pretty. Budgets vanish because finance saw us as a cost center.

Know what actually works? Stop trying to convince everyone. Start making them part of it.

Here's how I rally stakeholders without the corporate theater:

1. Anchor on one outcome, not 47 metrics

This campaign creates 30 meetings by March 31st.

Not impressions. Not MQLs. One number everyone understands.

2. Make ownership embarrassingly clear

Sarah owns email. Tom owns landing page. Mike owns enablement.

No we'll figure it out together BS. You own it or you don't.

3. Translate, don't escalate

Sales: This gets you 30 meetings
Finance: $50K investment, $500K return
Product: Positions feature X as differentiator

Same campaign. Three languages. Zero confusion.

4. Kill the weekly status meeting

Monday Slack update. Three bullets:
✅ On track
⚠️ At risk (why)
🔴 Blocked (need X)

2 minutes to read. No calendar invites.

5. Make fast decisions when shit gets messy

Sales wants A. Product wants B. Here's the tradeoff. I recommend A. Deciding by 3pm.

No committee. Just clarity.

6. One doc to rule them all

Not 14 decks. One living document:
Goal. Owners. Timeline. Status.

7. Bring sales in before you build

What would make this actually useful?

They shape it = They sell it.
They're surprised = They sabotage it.

8. Share wins like your job depends on it

That campaign? 12 meetings. $2M pipeline. Here's what worked.

Public wins create believers.

The brutal truth?

Your stakeholders don't care about your marketing strategy. They care about their problems.

Show them how you solve THEIR problems, and they'll fight for your budget.

Show them another PowerPoint, and they'll find reasons to say no.

I spent years trying to educate stakeholders about marketing.

Now I just show them what's in it for them.

Works every damn time.

LinkedIn's year in review was like getting a participation trophy from your kid's soccer league.

Congrats! You existed on our platform!

Meanwhile, ŌURA just dropped me 18 shots of actual data. Not 3. Not 5. EIGHTEEN. 

242,792 steps. 131 crowns. Sleep scores. Recovery trends. Stress patterns over time. And that's just what I could screenshot before my thumb got tired.

The kind of data that makes you go holy shit, I did that?

Not you posted 47 times or whatever vanilla metric LinkedIn thinks matters.

Here's what kills me about year in reviews:

Most companies treat them like automated birthday cards.

Generic. Forgettable. Zero emotional connection.

But when you show me I walked the equivalent of Boston to Philly and back? That I earned 131 daily crowns for hitting my goals? That my sleep improved when I started that evening routine?

That's not a recap. That's a mirror.

The companies that get this right understand something simple:

Data without context is just numbers.
Data with YOUR context is a story.

Spotify doesn't just say you listened to music. They show you discovered 847 new artists and played that one embarrassing song 97 times at 2am.

Strava doesn't say you exercised. They show you climbed the equivalent of Everest twice.

Oura doesn't say you wore a ring. They show you exactly how your body responded to every decision you made this year.

Why this matters for every company:

Your customers are doing incredible things with your product. But you're sending them PDFs that say thanks for being a customer.

Show them their journey. Their growth. Their wins they didn't even know were wins.

Make them feel something about their own progress.

4 years as an Oura customer (not sponsored but seriously, Oura, let's talk 👀) and this is the first year in review that made me actually proud of data.

Not because the numbers were good.

Because they told MY story.

Your move, LinkedIn. Maybe next year show me which posts actually moved someone's career forward instead of you got 73 reactions.

Until then, I'll be over here staring at my 242,792 steps wondering how my knees still work.

What's the best year in review you've gotten? The one that actually made you feel something?

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The Battle

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Nick Bennett

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