TomTalks?? with Brandon Taylor: Scaling Success Through People, Process, and Systems

In today's TomTalks?? interview, I sat down with accomplished revenue & sales leader Brandon Taylor to discuss his strategies for building and scaling high-performing sales organizations. Brandon brings a wealth of Chief Revenue Officer experience from his leadership roles at companies like FoodChain ID, Givewith, SaleXceleration, DigitalGlobe, and Drillinginfo.

Brandon shares his philosophy on motivating and retaining top sales talent, the importance of cross-functional alignment, optimizing pricing models, effectively integrating sales teams post-acquisition, leveraging AI in sales, improving sales velocity, expanding globally, partnering with marketing, and building trust with the board and executive peers.

With a proven track record of driving double and triple-digit growth, Brandon examines 12 key drivers to optimize companies for scale, from launching high-performing sales cultures and refining sales processes to identifying upsell opportunities and accelerating growth through the right talent, systems and KPIs.

Currently serving as a Board Member at The Gratitude Network and a Board Advisor at FuelTrust, Brandon remains passionate about leadership development and social impact.?

Let's dive into his wealth of experience and actionable insights! ??

Tom: Retaining top sales talent is a challenge, especially in competitive markets. What's your philosophy and approach to motivating, engaging and holding on to elite sales professionals?

Brandon: One of my all-time number one things to scale an organization is around talent and people. My passion for hiring sales talent is pretty big. It's not just about recruiting the right people, but it's as much about them buying into you as a leader. I take a passive approach to recruiting, interviewing two people a week regardless of whether I have an open position or not.?

The type of talent you want are those who are happy and performing well where they are, but you have a spot that's better for them with stronger leadership. I'm passionate about their career development. I want to know their five-year career plan in one page of bullet points, whether it's getting their masters, wanting my job, being CEO, or being the best salesperson at the company. I reverse engineer their plan into what they're doing today to make it worthwhile. If you can hire the right people, align their career plan, give them a strong swim lane and opportunity to make money and take care of their family, you'll keep them as long as you want.

Tom: You've led sales teams to impressive growth in multiple companies. What are the key elements of your approach to building and scaling a high performing sales organization???

Brandon: I believe in people, process and systems, in that order. You can start with the right people and make things happen even without perfect processes and systems. But systems and processes alone will fail without the right people.

To achieve double and triple digit growth, I align people, processes and systems in parallel to enable scaling. For example, in my current company, I hydrated our 27 products down to the 10 with the highest ASP, lowest CAC, most upside and shortest sales cycles. I built training and onboarding around those 10 in Highspot, hired the right people, gave them regional swim lanes, and created a comp plan incentivizing 3X commission on those 10 products.?

The result? We 3X'd our pipeline in Q1-Q3 and almost 3X'd in Q4. When you get the combination of people, process and systems right, it works.

Tom: Many CROs struggle with cross functional alignment. How do you ensure sales, marketing product and customer success are working in lockstep to drive growth?

Brandon: Alignment across the commercial organization, marketing, product and customer success is crucial but challenging, as different groups can move in misaligned directions, especially if they report into different leaders.?

What I've found effective is creating cross-functional leadership meetings involving all four groups to align priorities around a central growth number - e.g. $20M per quarter. I break that number down by sales region, product, marketing needs, and customer success goals. Someone, whether the CRO, CEO or CFO, needs to lead the alignment and create KPIs for each group tied to the overall goal.

It's critical to openly communicate and track progress on a monthly and quarterly basis to ensure continued alignment, as it's easy for groups to feel pressure and shift focus away from the holistic growth view. Regular tracking and alignment discussions are key to get everyone rowing in the same direction.

Tom: Pricing and packaging is critical for SaaS businesses. Can you share an example of how you've optimized a company's pricing model to accelerate revenue growth?

Brandon: At one SaaS company providing data analytics for the energy industry, we had a great product with 10,000 users across companies of all sizes. But the pricing was broken. For example, one large global company spending only $70K was using our data to inform billion dollar acquisition decisions, while a mid-size company was spending $400K.?

We had user-based a la carte pricing that allowed customers to churn users frequently. To fix this, we analyzed the value and segmented the pricing model into 10 tiers based on company size and value. Tier 1 was small companies up to 10 employees, while Tier 10 was enterprise giants. Pricing for the top tier went from $70K to $500K.?

After evolving the model, we enabled our sellers to resell the product's value to VPs, directors and C-level execs. In the first year, we didn't get the full $500K from the major client, but we did secure $1.2M over 3 years, demonstrating the true value. We organized the sales team against the tiers with inside sales for Tiers 1-3, regular AEs for 4-7, and strategic AEs for 8-10.

We then took it to the next level, making that the basic product and layering on "plus" and "pro" versions to drive further growth with new product development and acquisitions. The pricing optimization unlocked strategic selling opportunities.

Tom: You've been through multiple successful acquisitions. What advice do you have for CROs on how to effectively integrate sales teams and go to market motions post acquisition???

Brandon: It's crucial for the CRO to be involved in any acquisitions to understand how they fit into the organization. The biggest challenge is often with top performers from small companies who suddenly become a small fish in a big pond after acquisition and can quickly become disengaged.

I've found success with a 3-month integration plan, starting with the CRO and commercial org meeting the acquired team on Day 1 to welcome them, lay out the integration roadmap, and make them feel part of the culture. I'm a firm believer in moving quickly to capture commercial synergies within the first 30 days vs waiting 6+ months.?

Over-indexing on communication, integrating them into the culture, and rapidly merging the commercial sales motions are the keys. Begin with the commercial integration in the first 30 days and then sequence the technology and operational integration after that. Making the acquired team feel valued and part of the team is critical.

Tom: Many sales leaders are exploring how Gen AI could impact selling. How are you thinking about leveraging AI to empower your sales teams to enhance the customer buying experience?

Brandon: I absolutely believe Gen AI will transform sales and marketing. The overall commercial budget may stay the same but how it's allocated will likely shift, perhaps to adopting AI-powered programs vs pure headcount expansion.

To figure this out, you can't just outsource it - you have to dig in and learn it yourself. I have a team evaluating different applications, from AI-assisted BDR outreach and marketing content generation to using AI for effective LinkedIn prospecting and audience engagement. We're looking at how to leverage Gen AI to lower customer acquisition costs, boost conversion rates and accelerate pipeline and revenue.

I'm attending conferences and networking with other CROs to learn how they are applying Gen AI to enhance growth. The most successful commercial leaders will be those who embrace Gen AI and learn how to harness it, not to replace sellers, but to augment their capabilities in acquiring customers and driving pipeline. It's here to stay and will play an increasingly important role - the key is to start experimenting now.

Tom: Deal velocity is key to scaling. What are some of the most impactful ways you've found to improve sales cycle times and increase win rates?

Brandon: It starts with hiring the right people who understand and adhere to a rigorous sales process. No matter the company, a strong sales process should be the foundation. It typically involves 5 key stages, with qualification being critical. Reps need to identify the prospect's real pain, understand if they have budget to solve it, and know who the decision-makers are. That's a true qualified opportunity with a real chance to win.

Beyond people and process, having the right level of technical expertise to educate prospects is also key, especially in SaaS. It's telling that 40-60% of lost deals in SaaS are not to competitors, but to no decision - the buyer either didn't know enough, was overwhelmed with information, or perceived the purchase as too risky. That comes down to the salesperson not doing an effective job selling value and mitigating risk concerns.

Tom: You've expanded sales successfully in international markets for multiple companies. What are the keys to getting global expansion right from a sales leadership perspective?

Brandon: I've had some missteps here over the years so can share a balanced perspective. When expanding outside the US, you first have to assess costs, as it's usually easier to scale domestically with an existing footprint vs breaking into new geographies.

I've found success leading with channel partnerships when entering Latin America, EMEA or APAC, as that's often more cost-effective than direct hiring. Start with partners, get some wins, and then layer in regional employees over time as the business scales. The key is to identify the right regional sales leader for each geo who can build an effective partner ecosystem and drive revenue growth.

I also look for a clear path to profitability in each region within a reasonable timeframe, as international expansion can be a drag on growth if not managed prudently. Focus, partnerships and strong regional leadership are the keys to success.

Tom: Sales and Marketing alignment is a hot topic. How do you recommend CROs partner with their CMOs to maximize pipeline generation and revenue growth?

Brandon: Tight alignment between the CRO and CMO is absolutely critical to fueling growth, and often one of the most important internal partnerships to get right. The CRO is usually focused on people, process and systems, while the CMO drives global branding, demand gen and awareness - both are fundamental to revenue growth.

Like we discussed earlier regarding overall cross-functional alignment, I believe the CRO and CMO need to be joined at the hip with a weekly sync meeting. The CEO and board should see them working hand-in-hand with clear KPIs that link marketing's efforts to pipeline creation and closed/won revenue.

There's no magic formula, but a shared commitment between the CRO and CMO to put the company's growth objectives ahead of their individual functional priorities is the foundation. A rising tide lifts all boats - marketing and sales need to row together.

Tom: What's your advice to other CROs on how to build trust and credibility with their board and executive peers? How do you communicate sales performance effectively to key stakeholders?

Brandon: This is perhaps the most important topic we've discussed and should have been Question #1. If you don't get this right, you won't have the latitude to hire the right people, implement the right processes, or adopt the right systems.

When stepping into a new CRO role, I develop a 90-day plan evaluating growth levers across 12 key pillars. I hone in on the top 5 factors that can make the biggest near-term impact on revenue and build a plan to aggressively attack those 5 areas. I then over communicate the plan, my rationale, and my progress against it to the board and my executive peers. Initiatives need to be grounded in numbers and tied quantitatively to revenue impact - gut instincts are not enough.

For example, we recently hired a new rep and I was able to justify the high OTE we offered by showing the revenue impact the hire would drive based on deal sizes, sales cycle and quota attainment expectations. The numbers told a clear story.

You have to do this across the entire commercial org - with reps, with marketing programs, with training and enablement. Tie it all to revenue impact with clear metrics. Leverage data to guide decision-making and reinforce your judgment. Always anchor back to the core KPIs that ladder up to revenue and pipeline growth.

And fully own the number - hit it out of the park and you'll quickly gain trust. If you miss, provide clear explanations grounded in data and put forth a strong action plan to get back on track. Transparent communication, a firm handle on the business, and a results orientation will earn the trust of the board and your executive team. It's the foundation for success in any CRO role.

Thanks, Brandon! ??

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Tom Popomaronis is Co-Founder and Chief GenAI Officer at Phantom IQ . In addition to serving as a fractional GenAI consultant and experienced product innovator, Tom is a prolific writer and content strategist, having published over 1,000 op-eds across mainstream platforms including Entrepreneur Magazine, CNBC, Inc., and Forbes, while also enabling the publication of an additional 3,000+ op-eds for executive clients.