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About Brian Wolff

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So far Brian Wolff has created 10 blog entries.

The Accidental Sales Rep

The Accidental Sales Rep: How I Helped Run a $3M Business Without a Playbook Background: A Recession, a Reception Desk, and a Chance In 2009, fresh out of college and deep in the heart of the Great Recession, I landed an administrative gig at a leading plasticard manufacturer. It was nothing glamorous—just a 3-month maternity [...]

The Accidental Sales Rep2025-05-05T17:12:09-05:00

How the “Super Posting” Saved Sales

From $419 to $800: How the “Super Posting” Saved Sales at CareerBuilder Background: Competing With Ourselves CareerBuilder may now be a SaaS platform, but for much of its early success, it was built on a simple product: the $419 job posting. By 2013, that model became a problem. Customers could buy the same posting online—often [...]

How the “Super Posting” Saved Sales2025-05-05T17:10:58-05:00

From Chaos to Clarity

From Chaos to Clarity: How a New Sales Process Drove 400% Growth at Guerrero Howe Background: A Broken System Built on Overlap In 2013, Guerrero Howe operated a private publishing label focused on paid editorial content—featuring career stories of C-suite executives in industries like tech, law, and design. The model was straightforward: Interview executives for [...]

From Chaos to Clarity2025-05-05T17:08:08-05:00

Turning Bureaucracy Into Buy-In

Turning Bureaucracy Into Buy-In: How a Public University Signed Early for $120K Background: High Volume, Limited Resources, and a Familiar Face In Q2 2020, I began working with a Top 20 public university, focusing on SaaS solutions for Graduate Admissions. The decision-maker (DM) led admissions across the full university system, overseeing tens of thousands of [...]

Turning Bureaucracy Into Buy-In2025-05-05T17:06:07-05:00

Radical Honesty

“Why Would We Fail?” — How Radical Honesty Closed a $100K ABM Deal Background: First-Time Evaluation, Limited Access In 2018, I was working with a leading SaaS provider in human capital data as they evaluated ABM for the first time. The evaluation was championed by the VP of Marketing, who quickly became a trusted partner. [...]

Radical Honesty2025-05-05T17:03:35-05:00

From ‘No Access’ to In-Person Signature

From 'No Access' to 'In-Person Signature': How We Closed a $350K ABM Deal at Demandbase Background: A High-Stakes Buyer With No Clear Path In In Q3 2019, I prospected a Director of Marketing at a Minnesota-based SaaS company. Backed by CMO sponsorship, the company was exploring ABM software for the first time to meet aggressive [...]

From ‘No Access’ to In-Person Signature2025-05-05T17:00:56-05:00

Curiosity Beat the Script

From “Smile & Dial” to First SaaS Deal: How Curiosity Beat the Script at CareerBuilder Background: An Outdated Model in a Shifting Market In 2011, CareerBuilder was far from the HR tech platform it is today. The business relied almost entirely on selling resume database access and online job postings—with no software products on the [...]

Curiosity Beat the Script2025-05-05T16:57:50-05:00

Identifying Untapped Markets

Breaking the Mold: How an Untapped Market Became a Blueprint for Growth Background: A Narrow Focus, A Flat Pipeline In 2017, eMedia’s growth was stalling. Revenue heavily depended on renewing and expanding existing SaaS clients. Other industries—like manufacturing—were overlooked entirely, deemed “non-ICP,” and ignored in outbound efforts. New business within the ICP was hard to [...]

Identifying Untapped Markets2025-05-05T16:54:30-05:00

From Disqualified to Deal

From Disqualified to Deal: How One “Practice Lead” Sparked $200K in Revenue Background: Starting from Scratch In Q1 2018, I entered my first active quarter as an AE at Demandbase with one clear mandate: build my own pipeline. While I supported senior team members on inbound qualification, most leads were mine to generate. Then came [...]

From Disqualified to Deal2025-05-05T16:51:48-05:00

Reviving Revenue Through Relevance

Reviving Revenue Through Relevance: How We Changed the Game at 2XPAND Background: A Broken Status Quo In Fall 2022, I joined 2XPAND as the third executive hire, stepping into a lead generation and content syndication industry that had lost its edge. Customers were underserved. Relationships replaced problem-solving. ROI was weak. CSAT was low. Churn sat [...]

Reviving Revenue Through Relevance2025-05-05T17:20:45-05:00
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