SaaS Backwards - Reverse Engineering SaaS Success – Details, episodes & analysis

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Gifting can be a powerful outbound strategy that captures attention far more effectively than an email. 

In this week’s SaaS Backwards podcast episode, we spoke with Kris Rudeegraap, Co-CEO and Co-Founder at Sendoso, a gifting and direct mail platform that helps revenue teams 6x second call rates, double win rates, and close deals 29% faster.

Kris shared how his background in software sales and experience with gifting inspired him to create Sendoso. He provided insights into the company’s initial go-to-market strategy, its evolution from a "growth at all costs" mindset to a more efficient, profit-driven approach, and how this shift has shaped its success.

We also discussed common objections and misconceptions about gifting, such as it being “too expensive” or impractical without someone’s address—and how Sendoso addresses these challenges.

Kris backed up Sendoso’s impressive results with client success stories: Gong influenced over $30 million in pipeline by mailing pinatas, Guru improved meeting conversion rates by sending cupcakes, and Verkada saw a remarkable increase in ad conversion rates by offering a Yeti mug as a meeting incentive across social media and LinkedIn campaigns.

Read more Sendoso success stories here and view customer examples here. 

Key takeaways from this episode:

• The power of gifting as an outbound strategy
• How Sendoso helps clients select the right gifts for the right people at the right time
• Insights into the fundraising process and the current environment for startups

Other resources to check out:

Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publishes a yearly report about how B2B buyer behavior is changing.

The Lead Gen Mistake I Guarantee You’re Making – how to create content that better identifies intent from today’s b2b buyer.

And, if you want an outside look at your content with actionable advice, take advantage of our Content Audit. Valued at $20K in free consulting

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Building meaningful connections with individuals using different channels can be more effective than running an ABM program that only provides a shallow understanding of what’s happening within an account. 

In this week’s SaaS Backwards podcast episode, we spoke with Dmitri Lisitski, Co-Founder and CEO at Influ2, a person-based advertising platform that allows you to reach specific people within target accounts and see who interacts with your ads.

Dmitri takes us behind the scenes and discusses how his frustration with imprecise ABM platforms led to the creation of Influ2, which aims to solve this problem by targeting individual decision-makers within an account rather than only providing this broad view.

We discuss the orchestration between sales and marketing and the significance of nurturing relationships over time in enterprise sales. Dmitri explains how the best thing marketing can do for salespeople is target the same account they’re trying to chase and influence their decision, build awareness, and track intent. 

Our conversation also covers the role of thought leadership in generating conversations and supporting the sales process, the impact of AI on content creation, and attribution challenges in B2B marketing.

This episode provides valuable insights for SaaS CEOs, CMOs, and B2B marketing and sales professionals.

Key takeaways from this episode:

• The humanization of sales and marketing in the enterprise motion
• Why the use of AI in content development falls flat and what to do instead
• Measuring the impact of advertising on revenue

Other resources to check out:

Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publishes a yearly report about how B2B buyer behavior is changing.

The Lead Gen Mistake I Guarantee You’re Making – how to create content that better identifies intent from today’s b2b buyer.

And, if you want an outside look at your content with actionable advice, take advantage of our Content Audit. Valued at $20K in free consulting

---

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Your messaging could be turning buyers away before you even get a chance to pitch.

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We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations.

And the best part?

💡 It’s completely free.

No commitments, no pressure—just actionable advice to help you book more demos.

Your next demo is just a click away—claim your free review now.

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Listen, assess, plan, execute, iterate. This week’s podcast guest Janet Jaiswal outlines these as the essential steps in developing and implementing successful marketing strategies in the SaaS industry.

Janet Jaiswal is Blueshift's Global VP of Marketing and has 20 years of experience in B2B SaaS marketing, working with companies like IBM, eBay, and PayPal. 

In this episode of SaaS Backwards, she discusses her expertise in scaling companies through effective go-to-market strategies and the importance of process, technology, and skill sets at different stages of a company's growth. 

In our conversation, Janet provides insights into the relationship between SEO and content marketing, the importance of identifying and refining the Ideal Customer Profile, and the critical role of product marketing in driving alignment between marketing and product management. 

Overall, this episode provides a comprehensive look at the strategies and tactics that SaaS marketing leaders can use to drive growth and enhance profitability for their organizations.

Key takeaways from this episode:

• The changing landscape of search engine algorithms and the importance of prioritizing content that conveys value quickly
• The challenges and opportunities of ICP expansion and insights into the process
• Why product marketing is crucial when scaling a SaaS company

More Resources from Janet Jaiswal:

• Masterclass on Product Marketing: A deep-dive into Product Marketing for B2B SaaS scale-ups
• Defining your ICP: Discover the optimal approach to identifying your true target market

Other resources to check out:

Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publishes a yearly report about how B2B buyer behavior is changing.

The Lead Gen Mistake I Guarantee You’re Making – how to create content that better identifies intent from today’s b2b buyer.

And, if you want an outside look at your content with actionable advice, take advantage of our Content Audit. Valued at $20K in free consulting

---

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Your messaging could be turning buyers away before you even get a chance to pitch.

🔗 Get a Free Messaging & Conversion Review

We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations.

And the best part?

💡 It’s completely free.

No commitments, no pressure—just actionable advice to help you book more demos.

Your next demo is just a click away—claim your free review now.

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It seems like lead generation has become the Red-Headed stepchild of modern marketing. But it’s certainly not going away—especially since most SaaS companies have built their sales and marketing infrastructures around it.

It does need to evolve though, and that was the gist of our discussion with Cristina Daroca, Senior Director of demand marketing at Riverbed Technology.

Leads are not created equal. 

For example, if someone wants a demo or to speak with sales, “Speed to lead” still applies. You should follow up with them as quickly as possible when they’re sales ready.

However, for content downloads of assets such as white papers, it’s not a good idea to annoy them with a quick phone call. Instead, try understanding where they are in their journey so you can provide the right assistance at the right time. 

Daroca also talks about how ABM and demand generation should not be separate functions and must work closely together. It’s when people start engaging with content where your ABM motion can start. 

Overall, lead generation and the lead funnel aren’t the problem. It's about how we evolve that to ensure that we're creating the demand so that when leads come in, they’re the ones we actually want. 

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Like sales, marketers have a hard time with a product or service they don’t believe in. 

When Amber Bogie was searching for the right marketing opportunity, she was less concerned about the product and more concerned about joining a mission driven company. 

So, she developed a quadrant:

• What does the company offer as a product? 
• What is the company culture and how does that fit in with you?
• What is the role itself and how does that fit with how you want to grow?
• What kind of leadership does it have?

She found that at Reachdesk—a company committed to delivering customers and prospects a moment of delight and connection had the right mix.

Now three months into her new gig, Bogie is bringing a holistic view of the marketing and sales funnel where targeted demand generation fills the top, and once they enter the CRM, account-based touchpoints begin with channels and tactics creating a flywheel effect. 

And account-based experience (ABX) is the key piece to create the flywheel. Brand drives demand, ABX throughout the entire journey, and customer advocacy fuels back to the top. 

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Aligning with Sales is job one for David Gabriel, head of marketing for the fast-growing startup eVolve MEP.

“Sales has the hard job. They’re in the trenches and we want to do everything we can (as marketers) to make their jobs easier.”

That doesn’t mean that they aren’t looking at the long-term picture—they do many things that keep them in touch with their customers.

For example, they surveyed customers during COVID and found they were itching for group interactions. So they put together a Top Golf event, and it completely sold out. “If we’d followed the mainstream thinking on events we would have missed out on that opportunity.

Surviving at a startup requires serious agility combined with a north star of profitability and marketing ROI.

Gabriel achieves that by hiring “T-Shaped marketers,” which he defines as having a core skill but can also serve as utility players in all aspects of marketing. Depending on what sales is seeing determines what marketing focuses on - so the marketers have to be ready to pivot.

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Most companies do “checklist marketing” by default: We need to be on every social channel. We should have a newsletter for every customer segment. We need to go to all these conferences.

Fractional CMO Yasmin Morrison challenges her clients to think about marketing more like an investment portfolio and every quarter, you make bets. 

If it doesn’t pay dividends, get out. Double down if it does.

And you can put the odds massively in your favor if you apply the 80-20 rule (also known as the Pareto Principle) where a small percentage of activities drive a large percent of results.

For example, 20 percent of your web pages are driving 80 percent of your traffic. Or, 20 percent of your blog posts are driving 80 percent of your leads.

“Because SaaS companies collect a lot of data, they’re usually sitting on a gold mine,” she says.

After conducting market research for one client, she found that two out of 100 integrations had significantly more demand than all the others combined. 

They wrote one blog post on one topic and one use case. A month later, they had 10Xed their web traffic. 

Speaking in terms of marketing as an investment portfolio will also improve communications with the CFO—it’s language they understand.

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Having been with Refine Labs, MJ Peters knew how to sniff out the opportunity to work with a company that gets marketing. 

Now four months into her new gig as the VP of Marketing for CoLab Software, MJ talks about building a demand gen first marketing model where marketing is measuring only Sales Qualified Leads (SQLs) and Sales Accepted Opportunities (SAOs) as opposed to anything further up the funnel (like MQLs, content downloads, etc.) that’s normally tracked in the lead gen model. 

That’s still hard to do—the industry has problem awareness (engineer tools live on a desktop making it hard to collaborate efficiently) but making the case to do anything about it is still a tough sell. 

And it takes time. Demand gen happens more slowly than lead gen because you’re measuring lagging metrics instead of leading indicators. 

Leadership has the stomach for it though. They’ve invested heavily in customer research, and MJ sees the opportunity to create a category for “Design Engagement Systems” where people would eventually search more on that term, leading right to them. 

Given that most companies aren’t working with a blank slate, MJ also has advice for those that want to make the shift but can’t turn lead gen off overnight. 

And as long as they’re open minded, the right marketing leader can have a big impact. 

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Where most SaaS companies experience problems with the effectiveness of demand capture strategies, Paddle had the opposite problem—they weren’t focused on long-term customer creation. 

In the beginning, that was fine because they “were so busy and productive "Hoovering" up the in-market demand.”

Davies says that as a CMO, you always carry two time frames in your mind. One which is this quarter and next, making sure you’ve got a full pipeline, and the second timeline, which is how we’ll be positioned two years from now and how we’re warming them up now for future sales. 

Some just aren’t ready now, and you don’t want to lose them in the future. 

Another problem was messaging. Salespeople were stumbling around explaining the company’s mission to their customers. 

Davies set out to change the overall company narrative to fit more in line with the Challenger Sale where you reframe the problem for prospects so that they’re looking at this problem in an entirely new perspective and bring them along for the journey. 

“That results in a much easier sale whether they’re with sales or self-serve, they can go faster with less friction because marketing has paved the first few roads for them.”

In other words, demand generation for Paddle is making sales easier, and Davies explains in a way that all SaaS companies can emulate.

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Getting specific about your ICP is an old saw—but why then aren’t more companies marketing efficiently?

Our guest, Annie Wissner, says the reason is because we’ve become too used to bull markets where you have wiggle room in marketing execution.

“We're still in that digital wave where it's primarily about Google Search, but there's a lot of other methodologies that can be utilized to get to customers and prospects in a much lower cost and effective manner.”

The times they are a changing—and those of us like Annie that have been through three recessions have a good idea about what comes next.

Bottom line, the companies that operate marketing with efficiency will thrive and those that don’t…

Well, don’t be in that category.

Check out this episode for some clear strategies you can execute on immediately.

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Not Getting Enough Demos?

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We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations.

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Your next demo is just a click away—claim your free review now.