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How to sell to $50m companies
YouTube Ads playbook, enterprise sales, Clay's Creator campaign, GIFs, ABM template, B2B podcasting & more...
Okerosi Davis
April 13, 2025 • Letter: 13 minutes
To Marketers,
Okerosi here with Product Weekly.
In this newsletter, I share proven insights I have gathered this week across; product marketing, B2B ad creatives & SaaS growth playbooks from the top 5% minds in the space.
In this week’s roundup:
- How to do YouTube ads
- Wynter workshops insights
- Outbound playbook (1k+ booked calls)
Weekly Letter
Clay’s product integration with LinkedIn Creators
If you haven’t seen it from your favorite LinkedIn Creators, go to the LinkedIn Search bar and type ‘ #Claypartner ‘, click ‘Post’ to filter.
With this, you will see the latest posts from Creators promoting Clay’s latest integration with influencer marketing platforms - Modash and Upfluence.
You can filter further by clicking‘ Date posted ‘ and selecting ‘ Past week’ only.
As I often write on here, B2B influencer marketing is becoming a pivotal distribution channel, more so on LinkedIn. Almost every week, I come across a Creator partnering with B2B SaaS brands in one form or another.
At a glance am seeing 10 Creators sharing the brand partnerships post, but one thing stands out from all of them: - Creative freedom
Some have done video posts, skits, and others have written text posts only.
Note: You can check this resource on B2B Influencer Marketing I put together at the beginning of this year. BTW, I am considering a 2.0 release soon with more example databases and drag & drop templates.
How Casey Hill spent $90k on B2B Creators
When Casey Hill was working at ActiveCampaign, he ran several B2B influencer campaigns ( insights in the resource linked above), and now, as the CMO of Dowhatworks, he is running a similar playbook but beyond social channels.
Yesterday, as of this writing, he shared the playbook on spending $90k with 18 influencers to drive revenue. Here are my notes from the LinkedIn post.
The biggest win: They worked with Rajiv Nathan on a performance deal partnership. Rajiv ran newsletter marketing workshops where folks had to get a trial to get in. This campaign generated over 30 trial signups and a ton of lessons to improve the next campaign.
The biggest misses:
No owned assets - my biggest bet for 2025 and beyond is the rise of serialized, owned content for brands. Get an army of influencers making podcasts, webinars, newsletters that you pay them to run but are owned by you (ie they make a podcast operated by you, under your company name, and you pay them $2k per episode they host and run)
Too much one-off - the problem with testing a 1-2 post pilot where the content angle isn’t super focused or done in tandem with other influencers is it’s next to impossible to track the impact.
Performance deals are tough - I like deals that set me up for a win-win and performance deals often do the opposite. An influencer can drive you 5m views and $500k in pipeline but if after 3 months you only have $8k in sales on a $30k target, you cut the deal.
The owned assets remind me of Cognism’s creator campaign programs, like partnering with Sales experts like Morgan Ingram to run a multi-content campaign, both owned (podcast series) and rented ( his social media channels). It’s a strategy worth thinking about.
Expert Webinar
How to sell to $50m companies - Wynter surveys’ analysis
I have written about Wynter surveys as shared by the founder, Peep Laja, from CMOs, CTOs, and CFOs on how they buy. You can get the insights in the archived posts.
Today, I am sharing the insights both Peep and his Head of Revenue shared in a recent workshop on a YouTube video.
Peep shared his summaries in this LinkedIn post
Here are my summaries;
75% of C-suite execs shortlist vendors by asking peers first, then validating on review sites like G2 and TrustRadius, with AI tools catching up at 25% usage in 2024 for mapping major players.
Brand awareness is crucial for getting shortlisted in large categories with 20-100 similar tools; focusing solely on direct response ads harms brand awareness and reduces chances of top-of-mind referrals.
Generate word of mouth in communities like Pavilion and Exit 5 by being present in discussions, having happy customers share experiences, and forming relationships with community members.
C-suite buying process involves a champion (often a director or junior-level person) doing preliminary research and shortlisting, with the CTO or CMO signing off after due diligence and demos.
CFOs have veto power in 30% of deals, run 16% of end-to-end procurement for larger purchases, and are involved in all larger deals regardless of department, focusing on total cost of ownership and ROI calculations.
C-suite execs shortlist 3 vendors for demos based mainly on website differentiators before any direct interaction, highlighting the importance of a clear, unique value proposition on the website.
Interactive demos, sandboxes, and pre-login content are crucial for engaging C-suite buyers, as many are averse to logging in before evaluating the product.
C-suite execs prefer live demos with sales reps over email or chat for high ACV deals ($10K-$500K+/year), with the salesperson's personality and preparation significantly impacting the demo's success.
For mission-critical tools like CRM or cybersecurity, brand reputation is crucial; unknown vendors are not considered, while for less critical, lower-cost purchases under $20k, C-suite execs are more open to smaller brands.
C-suite execs check vendor websites for differentiators and social media for signs of company viability, with an active founder presence on social media being a valuable asset for building credibility.
Content marketing is high-leverage for solo founders going upmarket; repurpose video into text for LinkedIn and podcasts, and build a personal brand and influence where customers congregate to establish trust and authority.
Proven Framework
B2B video podcasting report for 2025 ( 75+ shows)
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B2B podcasting is another distribution channel I am keeping close tabs on. This week, I came across a report from Sergrey Ross, Creative Director of Sway 1, worth noting.
Sergrey mentioned sharing the full report, but I was too early to comment on it. However, here is my analysis from the document file linked above from his LinkedIn post.
31% of the weekly podcast listens happen on YouTube, beating both Apple and Spotify.
90% of the top-performing podcasts feature CEOs or executive hosts
High-quality thumbnails get 3- 4x more views.
Industry terms in the titles generate 65.9x more views
Multi-format shows have 2x more viral potential
4 Examples of B2B podcast ads
Like I month ago, I wrote about B2B podcasting on my LinkedIn. I am looking to do a growth playbook in the space. Here is a LinkedIn post-extract covering the example campaigns.
1. Grammarly
Company: writing assistant software tool
Ad format: audio only
Message: writing can help forge strong relationship at work
Offer: 20% discount to those who upgraded
The impact:
- 6% website conversions
- 1200+ premium upgrades
- 152% return on ads spend
2. IONOS
Company: web-hosting provider
Ad format: audio & video
Message: repurposing the already campaign airing on TV & radio for awareness and clicks
Offer: giving the audience products capabilities for consideration
The impact:
- 0.38% click-through rate for audio
- 1.21% click-through rate for video
3. Klarna
Company: fintech for BNPL
Message: it's good to talk about money
Offer: Money Talks card game
The impact:
- 29% brand lift with association to 'positive money conversations'
- 19,000 wait list for physical copy of the game
- 36 minutes dwell time
- 3.1m attention/reach
YouTube Ads for B2B
YouTube ads for B2B, more so SaaS, are very underutilized as of now. This week, I came across Chris Chambers’ post on LinkedIn sharing YouTube ads insights.
Combining with my previous analysis on the topic from experts like Kamil, founder of 42 Agency, and Silvio Perez, co-founder of AdConversion, I wrote a post on how to invest in this ad space.
In the video clip below, Silvio says it YouTube ads cause the Halo Effect.
After running the ads for a given period, you are likely to a general lift in the following metrics;
- branded search campaigns
- overall organic traffic
Kamil adds that YouTube is a great tool for brand marketing - to help capture brand mind share.
YouTube video ad breakdown - Monday.com
A simple Thought Leaders Ads strategy
We’ve been running thought leader ads (TL Ads) on LinkedIn for 6 months (testing text, static images, and video).
Here’s what we found:
→ Video TL Ads (5 min>) drive 20x more views & 3x higher completion rates
→ They outperform static images & text-based TL Ads by a huge margin
Why?
1. LinkedIn’s algorithm prioritizes video content → More reach at a lower cost
2. Longer videos = Higher intent viewers → Those who watch are genuinely interested
3. Educational over promotional content → Builds trust instead of feeling like an ad
The best thought leader Ad strategy.
1/ Use a profile with the highest ICP following
→ Someone your audience already trusts = higher engagement & credibility
2/ Create video content that actually shows how your product works
→ No generic “why” videos. Show them the “how” (live demos, workflows, real use cases)
3/ You don’t need a fancy video setup
→ Simple, Loom-style videos (demos, interviews, raw insights) work just as well as high-production videos.
Most founders who try LinkedIn ads run product ads too soon.
These fail because they scream “BUY NOW” instead of “Here’s something valuable”
Key takeaways:
👉 Video TL Ads (5+ min) > Images & text
👉 Focus on showing, not just telling
👉 Use a profile with the right audience
If you’re running LinkedIn ads, stop burning the budget on static content.
Shift to long-form video TL Ads instead.
B2B Creatives
Example SaaS Email GIF - product launch
Check 6 more GIF email creatives here
Letter Examples
7 Tips to Enterprise Sales - VP GTM @ Hockeystack
3. Invest in customer success
CS can be a huge differentiator. A product can only go so far without top-tier customer success. HockeyStack as a product can do a lot of things, but being able to dedicate resources to enable our customers and build long-term relationships was key.
4. Multi-thread (you know this)
Bigger the company, bigger the buying group, longer the cycle.
Use the C-Suite or your investors for executive outreach/to join calls. Make introductions to existing customers/references. Add prospects on Slack/text. Build trust with procurement and security. Each positive interaction increases your chances and builds familiarity in the conversations you can’t be in.
5. Have a Real Champion
You need a true champion - someone who is willing to make intros, strategize on talk tracks for different stakeholders, and give you information/advice on how to progress the deal. Smaller companies may buy the product regardless, but in enterprise, you need someone who can sell you just as much as you are.
8 Pillars to ABM - cheatsheet from Vladimir Blagojevic
Content formatting process (50m views) - Pierre Herubel
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That is all for this week.
Reply to this email; questions & feedback.
Let’s connect via LinkedIn - Okerosi