Enterprise AE Quota Attainment seems significantly more challenging than Mid Market at Showpad - why is that?

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Accepted Answer

Former Sales Director perspective:

Showpad shifted their focus from Mid-Market first to Enterprise about 2 years ago. They were exclusively a mid-market player that enjoyed healthy but not exponential growth. Their two original co-founders were happy with where the company was but it appeared like the lead investor was not given they had fallen quite a bit behind Highspot & Seismic on both product features & market share.

In order to bridge the chasm they brought on a new CEO, CPO, CSO, CRO, CMO - the only c-suite to stay in place was their CFO (who is a world-class CFO)

However, the change in exec leadership led to three problems:

1) The product roadmap stalled: As said above, the product was competitive within mid-market but lacked major feature & functionality compared to Seismic & Highspot. The new CPO, who on paper looked like a smart hire coming from Miro, struggled to grasp the sales enablement market and created a revolving door of product & engineering talent that led to zero new features being created in his tenure. Today Showpad is likely in 5th place behind the two major players, Seismic & Highspot, as well as Allego & Bigtincan.  It's not competitive in the enterprise space and until they change CPOs I don't think it will

2) unrealistic sales goals: The sales cycle at showpad is between 3-6 months for mid-market buyers. Quotas for Enterprise deals were set in a similar time but forecast at closer to 3-months. In short, the whole sales org missed budget badly (in 2021 & 2022). This was coupled with an absentee CMO and lack of marketing strategy so pipeline coverage was often below 2x for Ent. Lack of success was largely focused on individual AEs. I was shocked when I was asked for names on my team to let go when it was my responsibility to make sure they were successful. Which brings me to point 3.

3) culture collapse: the original founders had created a brilliant culture. Yes, it was not the most economically efficient however people by and large loved the company, including me. The change in c-suite leadership turned the culture toxic relatively quickly. The CEO had come up through the ranks at Showpad and was neighbors with one of the co-founders. He had never been a CEO and was publicly struggling with imposter syndrome during company-wide calls. The best example would be comparing him to Joffrey Baratheon of Game of Thrones. A cruel kiss-the-ring culture was rewarded. While I was always treated well - the behind closed doors conversations were incredibly toxic and incompetent to the level of comical. Great talent become hard to keep.

In a nutshell:
- The product is not an Ent product and there is no product roadmap to get them there
- The sales incentive structure is not supportive to Ent buying cycles
- The culture rewards kissing the ring over sales performance. An Ent AE never hit quota while I was at Showpad and I don't see that changing without a new exec team

My advice if you're interested in the Sales Enablement space is to look at Seismic (great product, ok culture). I would avoid Highspot (Bro culture). Allego has an interesting product as well and may be worth checking out, no idea on their culture.

Answer

They don't know how to sell to the enterprise and have very junior sales reps that don't understand the enterprise space

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Enterprise AE Quota Attainment seems significantly more challenging than Mid Market at Showpad - why is that?