Crew Capital recently hosted a roundtable discussion led by Frank Golden, founder of Golden Ventures and experienced early-stage go-to-market (GTM) advisor. The session focused on scaling sales operations for startups that are transitioning beyond founder-led sales to building a GTM team — a critical inflection point in a company’s trajectory.

Frank brings deep expertise from over a decade in the startup ecosystem, where he helped scale four companies at seed stage — twice as the founding account executive, and twice as the founding sales leader. His sales experience spans companies like RelateIQ and Airkit (both acquired by Salesforce), as well as Talkdesk (Most recently valued at $10B from their $230M Series D).

Today, Frank & team have advised over two dozen startups with Golden Ventures, where they helps founders establish effective sales practices and build the foundations for scalable GTM operations. Their guidance helps companies navigate the crucial transition from acquiring the very first customer to building repeatable sales processes.

Throughout our roundtable, Frank shared practical insights on calculating necessary pipeline coverage, creating effective sales playbooks, and strategically sequencing sales hires. His data-driven approach offers founders a roadmap for scaling their sales teams while maintaining momentum and efficiency.

Calculate pipeline coverage using the win rate formula

When scaling a team from one sales representative to multiple, ensuring sufficient pipeline becomes a critical challenge, according to Frank.

“The first question is how much pipeline do you need? A lot of founders don’t pay attention to this,” he said. “That number, every founder should know this cold, is the inverse of your win rate – this is the pipeline coverage you need to hit your goals.” For example, if a company’s quarterly goal is $100,000 and its historical win rate from qualified opportunity to closed deal is 25%, it needs 4x coverage — $400,000 of pipeline — to reliably hit its target.

Frank also stressed that win rates should be at least 15% to maintain a healthy sales funnel. “If it’s not higher than 15%, your funnel is leaky and you’re going to spend too much time on deals that are never going to close” he said. Lower win rates require unrealistic pipeline coverage of 6-8x, making growth targets nearly impossible to achieve.

This insight sparked immediate recognition from one CEO in attendance who confirmed seeing similar conversion metrics in his company’s outbound efforts. For early-stage companies struggling with low win rates, Frank recommends a thorough reexamination of their ideal customer profile (ICP) and sales execution, rather than simply trying to generate more pipeline. Focus in the early days is key. 

The evolution of outbound sales

As companies scale their sales teams, they face increasing pressure to generate sufficient leads. Frank noted a significant shift in the GTM landscape that founders should recognize when planning their growth strategies.

“My advice to a lot of my clients these days is to invest in marketing earlier than you would have 5 years ago because outbound has gotten harder,” he said.

This recommendation stems from Frank’s observations about diminishing returns in traditional outbound prospecting. While outbound remains essential, its effectiveness has declined significantly, in part due to the barrage of AI-written emails that flood our inboxes every day.

“Best-in-class positive response rates on outbound multi-channel sequences like email, phone, calling, and LinkedIn is around 2%,” Frank said. “If you put 100 people in a sequence and 2 come back saying ‘I’ll take a meeting.'” Even after securing those meetings, companies typically convert only about half of those into qualified opportunities.

To combat these challenges, Frank recommends diversifying lead generation strategies across multiple channels simultaneously. “The short answer is you’ve got to be doing everything. You’ve got to be doing outbound, marketing, conferences, and if you have a partnership play, lean into that too,” he said. “With that said, partnerships can be a huge waste of time in the early days if you’re chasing partners that aren’t going to be great fits.”

For companies first beginning outbound efforts, Frank suggested LinkedIn automation as surprisingly effective when getting off the ground, despite it seeming counterintuitive in today’s oversaturated outreach environment.

“The lightest touch that works for a lot of our clients is LinkedIn automation,” Frank said. “We’ve turned it on for 10 clients. It’s worked for 8 of them.” His recommended approach is straightforward: Add prospects as connections without a note, then upon acceptance, send a brief message with an interest-based call to action. When prospects respond, move the conversation to email immediately.

Frank noted that while AI companies face the same fundamental GTM challenges as other traditional SaaS businesses, they often benefit from heightened market interest that can be leveraged. “For AI startups specifically, the content marketing and thought leadership angles can be particularly effective right now,” Frank said. “Having your technical founders publish detailed explanations of your approach or comparisons to other models creates inbound interest that traditional outbound can’t match.”

Building your first sales playbook

Frank emphasized the importance of documenting what works through a basic playbook before bringing on additional sales representatives.

“Ideally you have a skinny v1 playbook of how the founder has done sales here and sold $500,000 to $1 million of annual recurring revenue (ARR),” he said. The playbook doesn’t need to be complex, it should cover fundamental elements: ICP, account targeting strategy, outreach methods, sales process stages, objection handling, and examples of successful communication.

“That’s from ‘Here’s our ICP, here’s our database of accounts, here’s how we get in touch with those accounts and what works,’ and then ‘here’s the deal itself with all the stages and questions to ask and materials to use,'” Frank said.

Including examples of effective communication is particularly valuable. Frank recommends creating “a library of what great looks like” with email templates and recorded calls that demonstrate successful interactions at each stage of the sales process. This resource helps new hires understand what drives success in the company’s specific context.

When one founder expressed concern about creating a playbook without significant sales experience, Frank pushed back on the notion. “I would challenge you to just think of it like you’re the only one that has sold this thing in the world. You’re the expert for now,” he said.

The playbook should be treated as a living document that evolves as the team learns. “Every new rep would get the same version of the playbook, and it’s their responsibility to identify things that are not updated,” Frank said, describing how his teams managed playbooks at previous companies.

Strategic hiring for sales teams

When expanding beyond founder-led sales, the sequence of hiring plays a critical role in structuring a successful team.

“I am of the belief that it’s always best to bring on account executives (AEs) before sales development representatives (SDRs) and have them try outbound before SDRs do,” Frank said. This approach ensures that experienced salespeople establish effective outbound methods before delegating prospecting to more junior team members.

Frank cautioned against a common mistake he’s observed in early-stage companies. “What doesn’t work is hiring an SDR and having them figure out how to do outbound successfully. That rarely ever works,” he said.

Instead, Frank recommends that founders establish their initial sales approaches, then bring on experienced AEs who can refine those methods before adding SDRs to the mix. This creates a natural progression where outbound tactics are tested and validated by experienced salespeople before being scaled through SDR work.

When hiring multiple representatives, Frank suggested bringing them on in pairs whenever possible. “Ideally you’re bringing on 1 and 2 together or 2 and 3 together,” he said. This approach provides benchmarking opportunities and creates healthy competition while building the team culture.

For founders evaluating when to expand their sales teams, Frank encouraged striking a balance between top-down modeling and practicality of performance. “A lot of people do top-down modeling on the stuff we need to hit $3 million ARR. Here’s the capacity model. Here’s how many AEs we need to hire,” he said. “While that’s good to have as a baseline, it needs to be rooted in reality.” That reality check comes from scrutinizing if sales representatives have full plates. “Look at their calendar and ask, ‘Are they maxing out capacity right now?’ are they pairing new meetings with the right amount of active opportunities they’re running?” Frank said.

Transitioning from individual contributor to leader

The evolution from a high-performing salesperson to an effective sales leader is a significant challenge, especially in fast-growing startups. Frank shared specific insights on avoiding common pitfalls during this pivotal transition.

“One common pitfall, and this is for both the founder and salespeople: Do not make it a team lead role,” Frank said. “Team lead roles are really hard. If they’ve earned the manager role, give them the manager role and let them manage fully and impact revenue.”

Frank explained that “team lead” positions often create an awkward middle ground where individuals are expected to carry their own quota while simultaneously managing others. This divided focus rarely works in early-stage companies trying to scale quickly.

For founders hiring their first AE, Frank recommends a complete handoff of sales operations responsibilities, rather than maintaining a split ownership. “I say the same thing to founders that hire their first AE. They’ll say, ‘I’m going to run some ops and they’re going to run some ops.’ I say, ‘No, hand over all of your ops to them.'” This clean transfer of responsibility allows the founder to focus on other areas of the business while empowering the sales leader to take real ownership. “You can still run them or lead them, but you need to hand over everything,” Frank said.

The distinction between management and leadership becomes particularly important as companies scale. True management authority creates accountability and clarity, whereas ambiguous leadership structures can create confusion and inefficiency. With clear management roles established, the next challenge becomes determining when those managers need additional team members to support growing demand.

Determine when to expand your sales team

Finding the right size for a sales team requires a nuanced understanding of rep capacity and usage. Frank advocates for a data-driven approach that looks past theoretical models.

“At the end of the day, the reality of capacity comes down to their calendars,” he said. This practical perspective focuses on how representatives are spending their time instead of leaning on abstract projections. Effective AEs should maintain a balance between active selling and pipeline generation. “I like to say the best AEs spend 10 to 20% of their time outbounding,” Frank said. “If it’s more than that, it’s an expensive resource to have outbounding that much.”

On the other hand, insufficient outbound activity can indicate a potential problem, too. “If it’s less than that, I would hope that their calendars are 6 to 10 meetings a day with clients and they just have no time to do outbound prospecting,” he said.

Frank recommends analyzing the number of active opportunities each rep manages as another key indicator of capacity. Depending on deal complexity and size, this could range from 10 to 50 active opportunities per rep. When reps consistently operate at the upper end of their capacity for both calendar utilization and opportunity management, it signals the right time to expand the team.

This balanced approach to capacity management helps companies avoid both premature hiring, which can strain resources, and delayed hiring, which can lead to burnout and missed opportunities. By focusing on these practical metrics, companies can make more informed decisions about when to scale their sales organizations.