I lasted about a week at home before hitting the road again. From now through the end of June, Krystal and I are traveling almost every other week. I'm in Chicago this week which many of you know is one of my all-time favorite cities. Great people, amazing weather (other than the winter), and some of the best food in the country. Our meals this week have prompted Krystal and me to finally launch our food blog/Instagram (Travel2Taste), but that is another story for another time.

To say it's been an interesting week is an understatement. Our rental car got smashed by a semi (don't worry... it was parked and we were having lunch inside), and we got to see Chicago Fire being filmed (Hi Mouch).

It's been a busy week for the entire RR team. Onboarding new clients, solidifying new partnerships, and mentoring new leaders.

I'm so thankful that I get to do what I love every day and thankful for you spending the next few minutes of your life with me.

Let's talk GTM.

Today's estimated reading time is 4 minutes.

On Deck

• Due Diligence: It's For More Than Just Funding
• Lessons Learned as a Fractional GTM Leader: The Upmarket Mirage
• Content We Can't Get Enough Of
• High Competition High Growth

Due Diligence: It's For More Than Just Funding

Due diligence has never been more critical in a landscape crowded with rapid innovation and fierce competition. As a company, we preach the importance of due diligence, not just as a routine checkpoint, but as a vital, two-way conversation that underpins every strategic decision. I want to dive deeper into why due diligence must be a reciprocal process, and how it comes into play for more than the traditional mindset of funding.

Diligence should be done when hiring new people, looking for a new role, hiring a contractor, accepting a new engagement as a contractor, vetting new products, and more.

We just wrapped up diligence on a potential client engagement. We were approached by a founder, let's call her "Jenny," who was grappling with significant GTM challenges. Jenny was eager to sign an engagement letter and for us to come in, manage the team, and fix what "she thought" the problems were.

True to our ethos, we proposed a mutual exploration phase before any commitments were made.

The Mutual Exploration Phase

Jenny and her team wanted us on board. We had several solid discovery calls and even met in person. Jenny thought we were the right team for the job. While most folks would have signed an agreement and then spent the next 2-4 weeks messing around with "more discovery," this isn't how we operate. We requested unrestricted access to all pertinent data—sales figures, customer feedback, marketing analytics, and operational systems. This was not about mistrust but about ensuring that we could provide tailored, impactful recommendations.

As we peeled back the layers of Jenny’s operations, this transparent exchange did more than just reveal the numbers; it provided context, highlighted inefficiencies, and underscored potential areas for immediate impact. This thorough vetting process allowed us to understand not just what the problems were, but why they persisted and how they affected the company’s broader goals.

We spent 10+ hours reviewing CRM data, listening to sales calls, digging through sales playbooks, validating messaging, and more. A friend of mine, who also happens to be a fractional CRO asked me why we would do this, puzzled that we would spend 10+ hours unpaid digging into a prospect's data. The answer is simple... We want to provide as much value as possible, as quickly as possible. To do that, we must differentiate between the "perceived" problem and the "actual" problem. The only way to do this in a way that allows us to tell a founder exactly how and where we can help is to get our hands dirty and go deep with the data.

The Power of Informed Recommendations

Armed with this comprehensive insight, we were able to draft a proposal that was not just a band-aid but a strategic plan designed to address core issues and leverage existing strengths. Our recommendations were precise and our proposed outcomes were measurable. We could do this effectively because the due diligence phase ensured we weren't working in the dark.

Challenging the Status Quo

This approach challenges the often one-sided perspective of due diligence. Typically, companies exert considerable effort to vet new hires or new partnerships from a position of safeguarding their interests. However, true due diligence is a dialogue. It's about both parties assessing fit, alignment of values, and the potential for mutual growth. When both sides are vetting each other, it sets the stage for a relationship built on transparency, trust, and aligned objectives.

The Benefits of Reciprocal Diligence

The benefits of this reciprocal diligence are manifold. For one, it minimizes the risk of surprises that can derail projects and sour relationships. It ensures that every stakeholder is not just aware of the challenges ahead but is prepared and equipped to tackle them. Furthermore, this practice fosters a collaborative environment where both parties feel valued and understood, which is crucial for long-term success.

Takeaways

For startups and established businesses alike, our experience with Jenny offers valuable lessons:

• Transparency is Key: Encourage open access to information as this can transform the quality of your interventions and strategies.
• Mutual Assessment: Ensure that due diligence is not just about vetting others but also about being open to evaluation. This reciprocity can reveal critical alignments or misalignments early on.
• Tailored Strategies: Use the insights gained from thorough diligence to craft strategies that are not just generic but are profoundly aligned with the specific context and needs of the business.

Lessons Learned as a Fractional GTM Leader

Each week in this section, we aim to bring you real-life lessons learned either by us or by one of the founders we work with. All names have been changed to protect the identities of others...

The Upmarket Mirage: A Cautionary Tale of Ambition Over Acumen

One of our VC partners reached out to me and asked us if we'd be willing to engage with a founder named Alex who helmed a thriving SMB-focused tech company called SlmConnect. SlmConnect had carved out a respectable niche, providing agile solutions tailored to small and medium businesses. Life was good, or so it seemed until Alex attended a San Francisco-based tech conference where tales of 'going enterprise' floated around like the promise of a winning Powerball ticket.

Captivated by the lure of bigger contracts and prestigious logos, Alex returned with a vision—to pivot SlmConnect to serve the enterprise market. Ignoring warnings from his own VP of Sales, investors, and multiple seasoned advisors, Alex mistook enthusiasm for strategy and set about retooling his entire sales process to capture the enterprise whale.

The Shift: From Agile to Agonizing

Alex’s first move was to revamp the sales playbook. Out went the streamlined, tried, and true sales motions the team had built over the years suitable for SMBs; in came complex, multi-layered sales cycles designed for enterprise behemoths. The sales team, once lauded for their quick closures and deep customer relationships, suddenly found themselves grappling with RFPs, extended procurement processes, and a maze of stakeholders. These were SMB/MM sellers by design (and experience) who had absolutely no idea how to run a complex enterprise sales cycle.

The Fallout: Sales Plummet and Reps Flee

The impact was immediate and brutal. Sales cycles stretched to uncomfortable lengths, and the quick wins that once buoyed morale were lost in a sea of stalled deals. The sales team, unaccustomed and untrained for this new battlefield, grew frustrated. The high-energy buzz that once filled SlmConnect’s offices gave way to a droning uncertainty. Within months, several of SlmConnect's top sales reps, feeling out of their depth and disillusioned, jumped ship. Mind you, these were reps that were all over-achieving quota.

The Customer Confusion: What Does This Product Even Do?

Meanwhile, SlmConnect’s loyal SMB customers watched in confusion as the product they loved ballooned with unnecessary features aimed at appeasing enterprise IT departments. The intuitive interface was buried under layers of complexity that made sense only in boardrooms of the Fortune 500. Customer support calls spiked, not with queries for expansion but with questions about functionality—customers wondered aloud, "What the hell does the product even do now?"

The Reality Check: A Return to Roots

As sales dwindled and customer satisfaction scores plummeted, Alex faced a stark choice: continue down this perilous path or execute a humbling about-face. Choosing the latter, Alex convened the remaining team for a no-holds-barred retreat. The consensus was clear and compelling—SlmConnect thrived when it solved specific problems for SMBs, not when it chased enterprise ghosts.

With renewed focus, Alex and the team stripped away the cumbersome features, simplified the sales cycle, and returned to their roots. They rebuilt the sales team with a focus on core strengths and customer intimacy. Slowly but surely, SlmConnect regained its footing in the SMB market.

Lessons Learned: The Grass Isn’t Always Greener

Alex’s venture into the enterprise market reads like a modern-day business fable, a tale of ambition clashing with reality. It serves as a poignant reminder that scaling a business isn’t about chasing bigger prey but about understanding and owning your niche.

For other founders dreaming of upmarket glory, here are the takeaways:

• Know Your Strengths: Understand what makes your product or service resonate with your current customers before seeking new markets.
• Prepare Thoroughly: If you decide to target a new segment, invest in the necessary training and restructuring to ensure your team is up to the task.
• Listen to Your Customers: They’re the first to know when your product starts losing its essence. Keep them in the loop and heed their feedback.
• Be Ready to Pivot: Agility isn’t just for startups. It’s crucial for any business that takes a wrong turn.

Ambition is a vital driver of business growth, but without due diligence and a deep understanding of what your business truly excels at, it can lead to ventures as mistimed and misplaced as SlmConnect’s brief enterprise escapade. Remember, in business, sometimes the most powerful move is knowing when to hold fast to your founding vision.

Content We Can't Get Enough Of

I've admired Mark Kosoglow for some time. Often referred to as one of the most brilliant minds in SaaS, he "gets it" more than most. As a leader who believes deeply in "people," this particular post hit home for me.

High Competition High Growth with Alexa Grabell

Alexa Grabell is the Co-Founder and CEO of Pocus. Pocus is mission control for your pipeline. Pocus brings together product usage and other intent signals (customer, community, marketing data) to surface top leads, enabling reps to act fast. Alexa’s passion for democratizing data for go-to-market teams began when she led sales strategy & operations at Dataminr, where she built internal solutions to power sales teams with data.

During today’s show, Alexa shares her secrets on:

• why high amounts of competition can actually be a GOOD thing
• how to approach funding and the mindset behind it
• when to leverage product-led growth vs traditional sales methods

Check out the show here.